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Journal articles on the topic 'Glycolipides – Structure'

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Published: 4 June 2021

Last updated: 2 February 2022

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WUHRER, Manfred, Sandra RICKHOFF, Roger D. DENNIS, et al. "Phosphocholine-containing, zwitterionic glycosphingolipids of adult Onchocerca volvulus as highly conserved antigenic structures of parasitic nematodes." Biochemical Journal 348, no. 2 (2000): 417–23. http://dx.doi.org/10.1042/bj3480417.

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Human Onchocerca volvulus infection sera were found to recognize zwitterionic glycolipids of O. volvulus and to cross-react with those of other parasitic nematodes (Ascaris suum, Setaria digitata and Litomosoides sigmodontis). By the use of an epitope-specific monoclonal antibody, zwitterionic glycolipids of all these nematode species were observed to contain the antigenic determinant phosphocholine. A hyperimmune serum specific for arthro-series glycolipid structures reacted with the various neutral glycolipids of all these nematodes, which demonstrated that their oligosaccharide moieties belonged to the arthro-series of protostomial glycolipids. These results indicated that arthro-series glycosphingolipids carrying, in part, phosphocholine substituents, represent highly conserved, antigenic glycolipid markers of parasitic nematodes. Three glycolipid components of the O. volvulus zwitterionic fraction were structurally characterized by matrix-assisted laser-desorption/ionization time-of-flight MS, methylation analysis and exoglycosidase treatment. Their chemical structures were elucidated to be phosphocholine-6GlcNAc(β1-3)Man(β1-4)Glc(1-1)ceramide, GalNAc(β1-4)[phosphocholine-6]GlcNAc(β1-3)Man(β1-4)Glc(1-1)ceramide and Gal(α1-3)GalNAc(β1-4)[phosphocholine-6]GlcNAc(β1-3)Man(β1-4)Glc(1-1)ceramide for the zwitterionic ceramide tri-, tetra- and penta-hexosides respectively. The ceramide composition was found to be dominated by 2-hydroxylated docosanoic (C22h:0), tricosanoic (C23h:0) and tetracosanoic (C24h:0) acids, and C17 sphingosine (Cd17:1) (where h is hydroxylated and d is dihydroxylated).

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Redman, C. A., P. Schneider, A. Mehlert, and M. A. J. Ferguson. "The glycoinositol-phospholipids of Phytomonas." Biochemical Journal 311, no. 2 (1995): 495–503. http://dx.doi.org/10.1042/bj3110495.

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The Phytomonas spp. are trypanosomatid parasites of plants. A polar glycolipid fraction of a Phytomonas sp., isolated from the plant Euphorbia characias and grown in culture, was fractionated into four major glycolipid species (Phy 1-4). The glycolipids were analysed by chemical and enzymic modifications, composition and methylation analyses, electrospray mass spectrometry and microsequencing after HNO2 deamination and NaB3H4 reduction. The water-soluble headgroup of the Phy2 glycolipid was also analysed by 1H NMR. All four glycolipids were shown to be glycoinositol-phospholipids (GIPLs) with phosphatidylinositol (PI) moieties containing the fully saturated alkylacylglycerol lipids 1-O-hexadecyl-2-O-palmitoylglycerol and 1-O-hexadecyl-2-O-stearoylglycerol. The structures of the Phy 1-4 GIPLs are: Man alpha 1-2Man alpha 1-6Man alpha 1-4GlcN alpha 1-6PI, Glc alpha 1-2(NH2-CH2CH2-HPO4-)Man alpha 1-2Man alpha 1-6Man alpha 1-4GlcN alpha 1-6PI, [formula: see text] Glc alpha 1-2(NH2CH2CH2-HPO4-)Man alpha 1-2Man alpha 1-6Man alpha 1-4(NH2-CH2CH2-HPO4-)GlcN alpha 1-6PI [formula: see text] and Glc alpha 1-2Glc alpha 1-2(NH2CH2-CH2-HPO4-)Man alpha 1-2Man alpha 1-6Man alpha 1-4(NH2CH2CH2-HPO4-)-GlcN alpha 1-6PI. [formula: see text] The Phytomonas GIPLs represent a novel series of structures. This is the first description of the chemical structure of cell-surface molecules of this plant pathogen. The Phytomonas GIPLs are compared with those of other trypanosomatid parasites and are discussed with respect to trypanosomatid phylogenetic relationships.

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Laffoon, J., C. Lesch, and C. A. Squier. "A transmission electron microscopic study of porcine stratum corneum treated with topical applications of glycolipid." Proceedings, annual meeting, Electron Microscopy Society of America 44 (August 1986): 266–67. http://dx.doi.org/10.1017/s0424820100142955.

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The mammalian epidermis forms a differentiated surface layer termed the stratum corneum (sc) which represents the principal barrier. It is now known that the permeability barrier is located in the intercellular region of the sc and consists largely of neutral lipids derived from glycolipids that are aligned to form a highly hydrophobic structure. It is possible that this barrier might be augmented by topical application of pure glycolipid, which could diffuse through the regions between the squarnes. We have examined this possibility by treating the backskin of pigs with glycolipids and then preparing the tissue for examination with the transmission electron microscope (TEM).

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Nagahori, Noriko, Kenichi Niikura, Reiko Sadamoto, Kenji Monde, and Shin-Ichiro Nishimura. "Synthesis of Photopolymerizable Glycolipids and their Application as Scaffolds to Immobilize Proteins with a Micron-Sized Pattern." Australian Journal of Chemistry 56, no. 6 (2003): 567. http://dx.doi.org/10.1071/ch02182.

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Photopolymerizable glycolipids incorporating ceramide- or amido-type linkers and able to form stable monolayers were efficiently synthesized by chemical and enzymatic methods. Glycolipid polymer films served as platforms for the immobilization of proteins through specific carbohydrate–protein interactions at the air–water interface. Carbohydrate-binding proteins deposited on the glycolipid film were observed by atomic force microscopy, which showed varying submicron-sized protein patterns such as dendrites, dots, and networks, depending on the lipid structure, membrane preparation process, and sugar density of the membrane. Surface plasmon resonance measurement confirmed that the subunit-type lectins immobilized on the glycolipid membranes exhibited the ability to interact specifically with carbohydrate ligands by using unoccupied binding sites.

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Warabi, Kaoru, William T. Zimmerman, Jingkai Shen, et al. "Pachymoside A A novel glycolipid isolated from the marine sponge Pachymatisma johnstonia." Canadian Journal of Chemistry 82, no. 2 (2004): 102–12. http://dx.doi.org/10.1139/v03-183.

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Crude extracts of the North Sea marine sponge Pachymatisma johnstonia showed promising activity in a new assay for inhibitors of bacterial type III secretion. Bioassay-guided fractionation resulted in the isolation of the pachymosides, a new family of sponge glycolipids. A major part of the structural diversity in this family of glycolipids involves increasing degrees of acetylation and differing positions of acetylation on a common pachymoside glycolipid template. All of the metabolites with these variations in acetylation pattern were converted into the same peracetylpachymoside methyl ester (2) for purification and spectroscopic analysis. Pachymoside A (1) is the component of the mixture that has natural acetylation at the eight galactose hydroxyls and at the C-6 hydroxyls of glucose-B and glucose-D. Chemical degradation and transformation in conjunction with extensive analysis of 800 MHz NMR data was used to elucidate the structure of pachymoside A (1). Key words: Pachymatisma johnstonia, marine sponge, pachymoside, glycolipid.

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Leutou, Alain S., Jennifer R. McCall, Robert York, Rajeshwar R. Govindapur, and Andrea J. Bourdelais. "Anti-Inflammatory Activity of Glycolipids and a Polyunsaturated Fatty Acid Methyl Ester Isolated from the Marine Dinoflagellate Karenia mikimotoi." Marine Drugs 18, no. 3 (2020): 138. http://dx.doi.org/10.3390/md18030138.

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A new monogalactosyldiacylglycerol (MGDG), a known monogalactosylmonoacylglycerol (MGMG) and a known polyunsaturated fatty acid methyl ester (PUFAME) were isolated from the marine dinoflagellate Karenia mikimotoi. The planar structure of the glycolipids was elucidated using mass spectroscopy (MS) and nuclear magnetic resonance (NMR) analyses and comparisons to the known glycolipid to confirm its structure. The MGDG was characterized as 3-O-β-D-galactopyranosyl-1-O-3,6,9,12,15-octadecapentaenoyl-2-O-tetradecanoylglycerol 1. The MGMG and PUFAME were characterized as (2S)-3-O-β-D-galactopyranosyl-1-O-3,6,9,12,15-octadecapentaenoylglycerol 2 and Methyl (3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenoate 3, respectively. The isolation of the PUFAME strongly supports the polyunsaturated fatty acid (PUFA) fragment of these glycolipids. The relative configuration of the sugar was deduced by comparisons of 3JHH values and proton chemical shifts with those of known glycolipids. All isolated compounds MGDG, MGMG and PUFAME 1-3 were evaluated for their antimicrobial and anti-inflammatory activity. All compounds modulated macrophage responses, with compound 3 exhibiting the greatest anti-inflammatory activity.

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Nimrichter, Leonardo, Monica M. Burdick, Kazuhiro Aoki, et al. "E-selectin receptors on human leukocytes." Blood 112, no. 9 (2008): 3744–52. http://dx.doi.org/10.1182/blood-2008-04-149641.

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Selectins on activated vascular endothelium mediate inflammation by binding to complementary carbohydrates on circulating neutrophils. The human neutrophil receptor for E-selectin has not been established. We report here that sialylated glycosphingolipids with 5 N-acetyllactosamine (LacNAc, Galβ1-4GlcNAcβ1-3) repeats and 2 to 3 fucose residues are major functional E-selectin receptors on human neutrophils. Glycolipids were extracted from 1010 normal peripheral blood human neutrophils. Individual glycolipid species were resolved by chromatography, adsorbed as model membrane monolayers and selectin-mediated cell tethering and rolling under fluid shear was quantified as a function of glycolipid density. E-selectin–expressing cells tethered and rolled on selected glycolipids, whereas P-selectin–expressing cells failed to interact. Quantitatively minor terminally sialylated glycosphingolipids with 5 to 6 LacNAc repeats and 2 to 3 fucose residues were highly potent E-selectin receptors, constituting more than 60% of the E-selectin–binding activity in the extract. These glycolipids are expressed on human blood neutrophils at densities exceeding those required to support E-selectin–mediated tethering and rolling. Blocking glycosphingolipid biosynthesis in cultured human neutrophils diminished E-selectin, but not P-selectin, adhesion. The data support the conclusion that on human neutrophils the glycosphingolipid NeuAcα2-3Galβ1-4GlcNAcβ1-3[Galβ1-4(Fucα1-3)GlcNAcβ1-3]2[Galβ1-4GlcNAcβ1-3]2Galβ1-4GlcβCer (and closely related structures) are functional E-selectin receptors.

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Galili, U., B. A. Macher, J. Buehler, and S. B. Shohet. "Human natural anti-alpha-galactosyl IgG. II. The specific recognition of alpha (1----3)-linked galactose residues." Journal of Experimental Medicine 162, no. 2 (1985): 573–82. http://dx.doi.org/10.1084/jem.162.2.573.

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A natural IgG antibody (anti-Gal) with alpha-galactosyl binding specificity has been found in large amounts (0.5 - 1.0% of serum IgG) in all individuals tested. It has been purified by affinity chromatography on a column of melibiose-Sepharose. In addition to its affinity for normal and pathological senescent human red cells, the antibody readily interacts with rabbit red blood cell (RRBC) glycolipids with alpha-galactosyl terminal residues. Two types (glycosidic linkages of 1----3 vs. 1----4) of rabbit red cells glycolipids with terminal alpha-galactosyl residues were tested for antibody binding. The antibody specifically bound to glycolipids with Gal alpha 1----3 terminal residues, and treatment of these glycolipids with alpha-galactosidase abolished binding. Hemagglutination inhibition studies with oligosaccharides of known structure also showed that the antibody binds specifically to glycoconjugates with an alpha 1----3 terminal galactose residue. Anti-Gal did not bind to a human B-active glycolipid, indicating that fucose-linked alpha 1----2 to the penultimate galactose prevents anti-Gal binding. The anti-Gal specificity for RRBC glycolipids also paralleled that of the alpha-galactosyl-specific Bandeiraea simplicifolia lectin. The possible reasons for the occurrence of this unique antibody in human serum are discussed.

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Palestini, P., M. Masserini, G. Bottiroli, et al. "Involvement of Glycolipid-Enriched Domains in the Transduction Mechanism of Neurotrophins in Cultured Neurons." Bioscience Reports 19, no. 5 (1999): 385–95. http://dx.doi.org/10.1023/a:1020208121454.

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Specialized domains, displaying a peculiar lipid and protein composition, are present within the plasma membrane of mammalian cells and play a pivotal role in fundamental membrane-associated events. Among lipids, sphingolipids (in particular glycolipids and sphingomyelin) are characteristically enriched within such domains. Moreover, a series of functionally related proteins is present, suggesting the involvement of these membrane structures in the mechanism of signal transduction and lipid/protein sorting. An increasing body of evidence suggests that domains are dynamic structures, and that their dynamic fluctuations can modulate the activity of domain-associated proteins through changes of glycolipid–protein interaction. Even if a large body of experimental investigation has been carried out on eukaryotic cells, only little attention has been paid to the neuron. The purpose of the present review is to summarize the observations implying a functional role of glycolipid-enriched domains in cultured rat cerebellar granule cells.

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Kniep, B., WA Flegel, H. Northoff, and EP Rieber. "CDw60 glycolipid antigens of human leukocytes: structural characterization and cellular distribution." Blood 82, no. 6 (1993): 1776–86. http://dx.doi.org/10.1182/blood.v82.6.1776.1776.

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Abstract Monoclonal CDw60 antibodies recognize glycolipid antigens with restricted surface expression on human leukocytes. They allow us to define new functional subpopulations of T lymphocytes and are able to induce costimulatory signals. In this report, we describe the molecular composition of CDw60 glycolipid antigens derived from different human leukocyte subpopulations. The glycolipids were isolated and their structures were identified by immunochemical methods. All molecules containing the CDw60 determinant were found in the disialoganglioside fraction. They were O-acetylated derivatives of the gangliosides II3 (Neu5Ac)2-LacCer (GD3), IV3 (Neu5Ac)2-nLc4Cer (DSPG), and VI3 (Neu5Ac)2- nLc6Cer (DSnHC), respectively. The most common CDw60 glycolipid antigen in human leukocytes was 9-O-acetyl GD3. In a comparison of various cell types, the highest concentration of 9-O-acetyl GD3 on a per cell basis was determined in granulocytes and in blood T lymphocytes, whereas B lymphocytes, thymus cells, and monocytes contained considerably smaller amounts of this molecule. Polar CDw60 antigens such as 9-O-acetyl DSPG and 9-O-acetyl DSnHC were only detected in granulocytes.

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Monoclonal CDw60 antibodies recognize glycolipid antigens with restricted surface expression on human leukocytes. They allow us to define new functional subpopulations of T lymphocytes and are able to induce costimulatory signals. In this report, we describe the molecular composition of CDw60 glycolipid antigens derived from different human leukocyte subpopulations. The glycolipids were isolated and their structures were identified by immunochemical methods. All molecules containing the CDw60 determinant were found in the disialoganglioside fraction. They were O-acetylated derivatives of the gangliosides II3 (Neu5Ac)2-LacCer (GD3), IV3 (Neu5Ac)2-nLc4Cer (DSPG), and VI3 (Neu5Ac)2- nLc6Cer (DSnHC), respectively. The most common CDw60 glycolipid antigen in human leukocytes was 9-O-acetyl GD3. In a comparison of various cell types, the highest concentration of 9-O-acetyl GD3 on a per cell basis was determined in granulocytes and in blood T lymphocytes, whereas B lymphocytes, thymus cells, and monocytes contained considerably smaller amounts of this molecule. Polar CDw60 antigens such as 9-O-acetyl DSPG and 9-O-acetyl DSnHC were only detected in granulocytes.

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Kostetsky, Eduard, Natalia Chopenko, Maria Barkina, Peter Velansky, and Nina Sanina. "Fatty Acid Composition and Thermotropic Behavior of Glycolipids and Other Membrane Lipids of Ulva lactuca (Chlorophyta) Inhabiting Different Climatic Zones." Marine Drugs 16, no. 12 (2018): 494. http://dx.doi.org/10.3390/md16120494.

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Increasing global temperatures are expected to increase the risk of extinction of various species due to acceleration in the pace of shifting climate zones. Nevertheless, there is no information on the physicochemical properties of membrane lipids that enable the adaptation of the algae to different climatic zones. The present work aimed to compare fatty acid composition and thermal transitions of membrane lipids from green macroalgae Ulva lactuca harvested in the Sea of Japan and the Adriatic Sea in summer. U. lactuca inhabiting the Adriatic Sea had bleached parts of thalli which were completely devoid of chloroplast glycolipids. The adaptation to a warmer climatic zone was also accompanied by a significant decrease in the ratio between unsaturated and saturated fatty acids (UFA/SFA) of membrane lipids, especially in bleached thalli. Hence, bleaching of algae is probably associated with the significant decrease of the UFA/SFA ratio in glycolipids. The decreasing ratio of n-3/n-6 polyunsaturated fatty acids (PUFAs) was observed in extra-plastidial lipids and only in the major glycolipid, non-lamellar monogalactosyldiacylglycerol. The opposite thermotropic behavior of non-lamellar and lamellar glycolipids can contribute to maintenance of the highly dynamic structure of thylakoid membranes of algae in response to the increasing temperatures of climatic zones.

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Thouvenel, Laurie, Gautier Prevot, Laura Chiaradia, et al. "The final assembly of trehalose polyphleates takes place within the outer layer of the mycobacterial cell envelope." Journal of Biological Chemistry 295, no. 32 (2020): 11184–94. http://dx.doi.org/10.1074/jbc.ra120.013299.

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Trehalose polyphleates (TPP) are high-molecular-weight, surface-exposed glycolipids present in a broad range of nontuberculous mycobacteria. These compounds consist of a trehalose core bearing polyunsaturated fatty acyl substituents (called phleic acids) and a straight-chain fatty acid residue and share a common basic structure with trehalose-based glycolipids produced by Mycobacterium tuberculosis. TPP production starts in the cytosol with the formation of a diacyltrehalose intermediate. An acyltransferase, called PE, subsequently catalyzes the transfer of phleic acids onto diacyltrehalose to form TPP, and an MmpL transporter promotes the export of TPP or its precursor across the plasma membrane. PE is predicted to be an anchored membrane protein, but its topological organization is unknown, raising questions about the subcellular localization of the final stage of TPP biosynthesis and the chemical nature of the substrates that are translocated by the MmpL transporter. Here, using genetic, biochemical, and proteomic approaches, we established that PE of Mycobacterium smegmatis is exported to the cell envelope following cleavage of its signal peptide and that this process is required for TPP biosynthesis, indicating that the last step of TPP formation occurs in the outer layers of the mycobacterial cell envelope. These results provide detailed insights into the molecular mechanisms controlling TPP formation and transport to the cell surface, enabling us to propose an updated model of the TPP biosynthetic pathway. Because the molecular mechanisms of glycolipid production are conserved among mycobacteria, these findings obtained with PE from M. smegmatis may offer clues to glycolipid formation in M. tuberculosis.

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IWAMORI, Masao, and Yoshitaka NAGAI. "Structure and Function of Glycolipids." Journal of Synthetic Organic Chemistry, Japan 50, no. 5 (1992): 464–78. http://dx.doi.org/10.5059/yukigoseikyokaishi.50.464.

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Broussard, Alex, Alyssa Florwick, Chelsea Desbiens, et al. "Human UDP-galactose 4′-epimerase (GALE) is required for cell-surface glycome structure and function." Journal of Biological Chemistry 295, no. 5 (2019): 1225–39. http://dx.doi.org/10.1074/jbc.ra119.009271.

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Glycan biosynthesis relies on nucleotide sugars (NSs), abundant metabolites that serve as monosaccharide donors for glycosyltransferases. In vivo, signal-dependent fluctuations in NS levels are required to maintain normal cell physiology and are dysregulated in disease. However, how mammalian cells regulate NS levels and pathway flux remains largely uncharacterized. To address this knowledge gap, here we examined UDP-galactose 4′-epimerase (GALE), which interconverts two pairs of essential NSs. Using immunoblotting, flow cytometry, and LC-MS–based glycolipid and glycan profiling, we found that CRISPR/Cas9-mediated GALE deletion in human cells triggers major imbalances in NSs and dramatic changes in glycolipids and glycoproteins, including a subset of integrins and the cell-surface death receptor FS-7-associated surface antigen. In particular, we observed substantial decreases in total sialic acid, galactose, and GalNAc levels in glycans. These changes also directly impacted cell signaling, as GALE−/− cells exhibited FS-7-associated surface antigen ligand-induced apoptosis. Our results reveal a role of GALE-mediated NS regulation in death receptor signaling and may have implications for the molecular etiology of illnesses characterized by NS imbalances, including galactosemia and metabolic syndrome.

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Hewald, Sandra, Katharina Josephs, and Michael Bölker. "Genetic Analysis of Biosurfactant Production in Ustilago maydis." Applied and Environmental Microbiology 71, no. 6 (2005): 3033–40. http://dx.doi.org/10.1128/aem.71.6.3033-3040.2005.

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ABSTRACT The dimorphic basidiomycete Ustilago maydis produces large amounts of surface-active compounds under conditions of nitrogen starvation. These biosurfactants consist of derivatives of two classes of amphipathic glycolipids. Ustilagic acids are cellobiose lipids in which the disaccharide is O-glycosidically linked to 15,16-dihydroxyhexadecanoic acid. Ustilipids are mannosylerythritol lipids derived from acylated β-d-mannopyranosyl-d-erythritol. Whereas the chemical structure of these biosurfactants has been determined, the genetic basis for their biosynthesis and regulation is largely unknown. Here we report the first identification of two genes, emt1 and cyp1, that are essential for the production of fungal extracellular glycolipids. emt1 is required for mannosylerythritol lipid production and codes for a protein with similarity to prokaryotic glycosyltransferases involved in the biosynthesis of macrolide antibiotics. We suggest that Emt1 catalyzes the synthesis of mannosyl-d-erythritol by transfer of GDP-mannose. Deletion of the gene cyp1 resulted in complete loss of ustilagic acid production. Cyp1 encodes a cytochrome P450 monooxygenase which is highly related to a family of plant fatty acid hydroxylases. Therefore we assume that Cyp1 is directly involved in the biosynthesis of the unusual 15,16-dihydroxyhexadecanoic acid. We could show that mannosylerythritol lipid production is responsible for hemolytic activity on blood agar, whereas ustilagic acid secretion is required for long-range pheromone recognition. The mutants described here allow for the first time a genetic analysis of glycolipid production in fungi.

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Li, Yali, Enrico Girardi, Jing Wang та ін. "The Vα14 invariant natural killer T cell TCR forces microbial glycolipids and CD1d into a conserved binding mode". Journal of Experimental Medicine 207, № 11 (2010): 2383–93. http://dx.doi.org/10.1084/jem.20101335.

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Invariant natural killer T cells (iNKT cells) rapidly produce effector cytokines. In this study, we report the first crystal structures of the iNKT cell T cell receptor (TCR) bound to two natural, microbial glycolipids presented by CD1d. Binding of the TCR induced CDR3-α–dependent structural changes in the F′ roof of CD1d; these changes resemble those occurring in the absence of TCR engagement when the highly potent synthetic antigen α-galactosylceramide (α-GalCer) binds CD1d. Furthermore, in the Borrelia burgdorferi α–galactosyl diacylglycerol–CD1d complex, TCR binding caused a marked repositioning of the galactose sugar into an orientation that closely resembles α-GalCer. The TCR-dependent reorientation of the sugar, together with the induced CD1d fit, may explain the weaker potency of the microbial antigens compared with α-GalCer. We propose that the TCR of iNKT cells binds with a conserved footprint onto CD1d, regardless of the bound glycolipid antigen, and that for microbial antigens this unique binding mode requires TCR-initiated conformational changes.

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Fiedler, K., and K. Simons. "Characterization of VIP36, an animal lectin homologous to leguminous lectins." Journal of Cell Science 109, no. 1 (1996): 271–76. http://dx.doi.org/10.1242/jcs.109.1.271.

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VIP36 was isolated from MDCK cells as a component of glycolipid-enriched detergent-insoluble complexes. The protein is localized to the Golgi apparatus and the cell surface, and belongs to a new family of legume lectin homologues in the animal secretory pathway that might be involved in the trafficking of glycoproteins, glycolipids or both. Here we show that VIP36 is N-glycosylated and expressed in organs abundant in epithelial cells as well as in non-epithelial organs. Our studies demonstrate that the recombinant exoplasmic/luminal domain of VIP36 binds Ca2+ and that the protein decorates internal membrane structures of MDCK cells in vitro that are distinct from the Golgi apparatus. This binding requires Ca2+ and can be specifically inhibited by N-acetyl-D-galactosamine. The recombinant protein was used for affinity chromatography. Glycopeptides obtained from [3H]galactose-labelled cells bind to VIP36 and can be eluted with N-acetyl-D-galactosamine. Our data imply that VIP36 functions as a lectin in post-Golgi trafficking.

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Cecutti, Christine, Bonaventura Focher, Bruno Perly, and Thomas Zemb. "Glycolipid self-assembly: micellar structure." Langmuir 7, no. 11 (1991): 2580–85. http://dx.doi.org/10.1021/la00059a031.

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Seddon, John M., Oscar Ces, Richard H. Templer, David A. Mannock, and Ron N. McElhaney. "STRUCTURE AND PHASE BEHAVIOUR OF SYNTHETIC GLYCOLIPIDS." Molecular Crystals and Liquid Crystals 402, no. 1 (2003): 77–84. http://dx.doi.org/10.1080/744816839.

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IWAMORI, M., and Y. NAGAI. "ChemInform Abstract: Structure and Function of Glycolipids." ChemInform 23, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199245303.

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Fukushi, Daisuke, Hiroshi Sakuma, and Kazue Kurihara. "2P275 Surface Force Measurements of Interactions between Glycolipids Monolayers(40. Membrane structure,Poster Session,Abstract,Meeting Program of EABS & BSJ 2006)." Seibutsu Butsuri 46, supplement2 (2006): S364. http://dx.doi.org/10.2142/biophys.46.s364_3.

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Hammami, Walid, Candy Quiroga Castro, Wilfried Rémus-Borel, Caroline Labbé, and Richard R. Bélanger. "Ecological Basis of the Interaction betweenPseudozyma flocculosaand Powdery Mildew Fungi." Applied and Environmental Microbiology 77, no. 3 (2010): 926–33. http://dx.doi.org/10.1128/aem.01255-10.

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ABSTRACTIn this work, we sought to understand how glycolipid production and the availability of nutrients could explain the ecology ofPseudozyma flocculosaand its biocontrol activity. For this purpose, we compared the development ofP. flocculosato that of a close relative, the plant pathogenUstilago maydis, under different environmental conditions. This approach was further supported by measuring the expression ofcyp1, a pivotal gene in the synthesis of unique antifungal cellobiose lipids of both fungi. On healthy cucumber and tomato plants, the expression ofcyp1remained unchanged over time inP. flocculosaand was undetected inU. maydis. At the same time, green fluorescent protein (GFP) strains of both fungi showed only limited green fluorescence on control leaves. On powdery mildew-infected cucumber leaves,P. flocculosainduced a complete collapse of the pathogen colonies, but glycolipid production, as studied bycyp1expression, was still comparable to that of controls. In complete contrast,cyp1was upregulated nine times whenP. flocculosawas applied toBotrytis cinerea-infected leaves, but the biocontrol fungus did not develop very well on the pathogen. Analysis of the possible nutrients that could stimulate the growth ofP. flocculosaon powdery mildew structures revealed that the complex Zn/Mn played a key role in the interaction. Other related fungi such asU. maydisdo not appear to have the same nutritional requirements and hence lack the ability to colonize powdery mildews. Whether production of antifungal glycolipids contributes to the release of nutrients from powdery mildew colonies is unclear, but the specificity of the biocontrol activity ofP. flocculosatoward Erysiphales does appear to be more complex than simple antibiosis.

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Nagata, Masahiro, Yoshihiro Izumi, Eri Ishikawa та ін. "Intracellular metabolite β-glucosylceramide is an endogenous Mincle ligand possessing immunostimulatory activity". Proceedings of the National Academy of Sciences 114, № 16 (2017): E3285—E3294. http://dx.doi.org/10.1073/pnas.1618133114.

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Sensing and reacting to tissue damage is a fundamental function of immune systems. Macrophage inducible C-type lectin (Mincle) is an activating C-type lectin receptor that senses damaged cells. Notably, Mincle also recognizes glycolipid ligands on pathogens. To elucidate endogenous glycolipids ligands derived from damaged cells, we fractionated supernatants from damaged cells and identified a lipophilic component that activates reporter cells expressing Mincle. Mass spectrometry and NMR spectroscopy identified the component structure as β-glucosylceramide (GlcCer), which is a ubiquitous intracellular metabolite. Synthetic β-GlcCer activated myeloid cells and induced production of inflammatory cytokines; this production was abrogated in Mincle-deficient cells. Sterile inflammation induced by excessive cell death in the thymus was exacerbated by hematopoietic-specific deletion of degrading enzyme of β-GlcCer (β-glucosylceramidase, GBA1). However, this enhanced inflammation was ameliorated in a Mincle-deficient background. GBA1-deficient dendritic cells (DCs) in which β-GlcCer accumulates triggered antigen-specific T-cell responses more efficiently than WT DCs, whereas these responses were compromised in DCs from GBA1 × Mincle double-deficient mice. These results suggest that β-GlcCer is an endogenous ligand for Mincle and possesses immunostimulatory activity.

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Watanabe, Motoko, Yutaka Aoyagi, Akihiro Ohta, and David E. Minnikin. "Structures of Phenolic Glycolipids from Mycobacterium Kansasii." European Journal of Biochemistry 248, no. 1 (1997): 93–98. http://dx.doi.org/10.1111/j.1432-1033.1997.00093.x.

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DeMarco, Mari L. "Three-Dimensional Structure of Glycolipids in Biological Membranes." Biochemistry 51, no. 29 (2012): 5725–32. http://dx.doi.org/10.1021/bi3003633.

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Stefaniu, Cristina, Ivan Vilotijevic, Mark Santer, Daniel Varón Silva, Gerald Brezesinski, and Peter H. Seeberger. "Subgel Phase Structure in Monolayers of Glycosylphosphatidylinositol Glycolipids." Angewandte Chemie International Edition 51, no. 51 (2012): 12874–78. http://dx.doi.org/10.1002/anie.201205825.

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GEROLD, Peter, Livia VIVAS, A. Solabomi OGUN, et al. "Glycosylphosphatidylinositols of Plasmodium chabaudi chabaudi: a basis for the study of malarial glycolipid toxins in a rodent model." Biochemical Journal 328, no. 3 (1997): 905–11. http://dx.doi.org/10.1042/bj3280905.

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Free and protein-bound glycosylphosphatidylinositols (GPIs) of the blood stages of the rodent malarial parasite Plasmodium chabaudi chabaudi AS were identified and characterized. TLC analysis of material extracted by organic solvents from metabolically labelled parasites revealed a distinct set of glycolipids. These glycolipids were identified as GPIs by specific chemical and enzymic treatments and by structural analysis of their glycan and hydrophobic parts. These analyses revealed that P. c. chabaudi AS synthesizes a set of GPI-biosynthesis intermediates and two potential GPI-anchor precursors exhibiting the following structures: ethanolamine-phosphate [(α1-2)mannose]mannose(α1-2)mannose(α1-6)mannose(α1-4)glucosamine-(acyl)inositol-phosphate-diacylglycerol (P. ch. α) and ethanolamine-phosphate-mannose(α1-2)mannose(α1-6)mannose(α1-4)glucosamine-(acyl)inositol-phosphate-diacylglycerol (P. ch. β). One of these GPI-anchor precursors (P. ch. α) possesses the same carbohydrate structure as the GPI membrane anchor of merozoite surface protein-1 from P. c. chabaudi AS.

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Shimada, Haruo, Naoki Nemoto, Yasuo Shida, Tairo Oshima, and Akihiko Yamagishi. "Complete Polar Lipid Composition of Thermoplasma acidophilum HO-62 Determined by High-Performance Liquid Chromatography with Evaporative Light-Scattering Detection." Journal of Bacteriology 184, no. 2 (2002): 556–63. http://dx.doi.org/10.1128/jb.184.2.556-563.2002.

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ABSTRACT Polar ether lipids of Thermoplasma acidophilum HO-62 were purified by high-performance liquid chromatography with an evaporative light-scattering detector. Structures of purified lipids were investigated by capillary gas chromatography, mass spectrometry, and nuclear magnetic resonance. Three types of ether lipids were found: phospholipids, glycolipids, and phosphoglycolipids. The two phospholipids had glycerophosphate as the phosphoester moiety. The seven glycolipids had different combinations of gulose, mannose, and glucose, which formed mono- or oligosaccharides. The eight phosphoglycolipids with two polar head groups contained glycerophosphate as the phosphoester moiety and gulose alone or gulose and mannose, which formed mono- or oligosaccharides, as the sugar moiety. Although gulose is an unusual sugar in nature, several glyco- and phosphoglycolipids contained gulose as one of the sugar moieties in Thermoplasma acidophilum. All the ether lipids had isopranoid chains of C40 or C20 with zero to three cyclopentane rings. The structures of these lipids including four new glycolipids and three new phosphoglycolipids were determined, and a glycosylation process for biosynthesis of these glycolipids was suggested.

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Malinina, Lucy, Margarita L. Malakhova, Alex T. Kanack, et al. "The Liganding of Glycolipid Transfer Protein Is Controlled by Glycolipid Acyl Structure." PLoS Biology 4, no. 11 (2006): e362. http://dx.doi.org/10.1371/journal.pbio.0040362.

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Moody, D. Branch, Mark R. Guy, Ethan Grant, et al. "Cd1b-Mediated T Cell Recognition of a Glycolipid Antigen Generated from Mycobacterial Lipid and Host Carbohydrate during Infection." Journal of Experimental Medicine 192, no. 7 (2000): 965–76. http://dx.doi.org/10.1084/jem.192.7.965.

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T cells recognize microbial glycolipids presented by CD1 proteins, but there is no information regarding the generation of natural glycolipid antigens within infected tissues. Therefore, we determined the molecular basis of CD1b-restricted T cell recognition of mycobacterial glycosylated mycolates, including those produced during tissue infection in vivo. Transfection of the T cell receptor (TCR) α and β chains from a glucose monomycolate (GMM)-specific T cell line reconstituted GMM recognition in TCR-deficient T lymphoblastoma cells. This TCR-mediated response was highly specific for natural mycobacterial glucose-6-O-(2R, 3R) monomycolate, including the precise structure of the glucose moiety, the stereochemistry of the mycolate lipid, and the linkage between the carbohydrate and the lipid. Mycobacterial production of antigenic GMM absolutely required a nonmycobacterial source of glucose that could be supplied by adding glucose to media at concentrations found in mammalian tissues or by infecting tissue in vivo. These results indicate that mycobacteria synthesized antigenic GMM by coupling mycobacterial mycolates to host-derived glucose. Specific T cell recognition of an epitope formed by interaction of host and pathogen biosynthetic pathways provides a mechanism for immune response to those pathogenic mycobacteria that have productively infected tissues, as distinguished from ubiquitous, but innocuous, environmental mycobacteria.

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Nainggolan, Irwana, Shahidan Radiman, Ahmad Sazali Hamzah, and Rauzah Hashim. "The Effects of Branched-Tail Structure of Surfactant on the Phase Behaviour of Alkylglucoside/Water/n-Octane Ternary System." Applied Mechanics and Materials 754-755 (April 2015): 944–49. http://dx.doi.org/10.4028/www.scientific.net/amm.754-755.944.

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Two glycolipids were synthesized to study the lyotropic behavior of these glycolipids in alkylglucoside/water/n-octane ternary system. These glycolipids have been distinguished based on the structure of alkyl chain (branched-alkyl chain and straight alkyl chain). 2-octyl-β-D-glucopyranoside (2-OG) and 2-ethylhexyl-β-D-glucopyranoside (2-EHG) were used as surfactants to perform two types of phase diagram. Phase behaviours investigated were phase behaviours of 2-OG/n-octane/water ternary system and 2-EHG/n-octane/water ternary system. Small angle x-ray (SAXS) and optical polarizing microscope were used as the instruments to study the lyotropic phase behaviour of these two surfactans in ternary phase diagram. Study the effect of branched-tail structure on the phase behaviour of glycolipids in ternary system is one of strategy to derive the structure-property relationship. For this purpose, 2-OG and 2-EHG were used as surfactants in the same ternary system. The phase diagram of 2-OG/water/n-octane ternary system showed rectangular ribbon phase and lamellar phase. The phase diagram of 2-EHG/water/n-octane ternary system showed wide region of lamellar lyotropic liquid crystalline in different ratio of weight composition. In 2-OG/water/n-octane ternary system, as more surfactant was added to the system, the interlayer spacing, d1 and scattering angle, a value increased, whereas in 2-EHG/water/n-octane ternary system, the d1 and a value decreased.

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Shiraishi, Tsukasa, Shin-ichi Yokota, Naoki Morita, et al. "Characterization of a Lactobacillus gasseri JCM 1131TLipoteichoic Acid with a Novel Glycolipid Anchor Structure." Applied and Environmental Microbiology 79, no. 10 (2013): 3315–18. http://dx.doi.org/10.1128/aem.00243-13.

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ABSTRACTWe determined the chemical structure of lipoteichoic acid (LTA) fromLactobacillus gasseriJCM 1131T. The repeating unit was comprised of glycerolphosphate and 2-alanylglycerolphosphate. The glycolipid anchor was tetrahexosylglycerol with two or three acyl groups. To our knowledge, this is the first demonstration of a tetrahexose structure in an LTA glycolipid anchor.

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Zajonc, Dirk M., Harald Striegl, Christopher C. Dascher, and Ian A. Wilson. "The crystal structure of avian CD1 reveals a smaller, more primordial antigen-binding pocket compared to mammalian CD1." Proceedings of the National Academy of Sciences 105, no. 46 (2008): 17925–30. http://dx.doi.org/10.1073/pnas.0809814105.

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The molecular details of glycolipid presentation by CD1 antigen-presenting molecules are well studied in mammalian systems. However, little is known about how these non-classical MHC class I (MHCI) molecules diverged from the MHC locus to create a more complex, hydrophobic binding groove that binds lipids rather than peptides. To address this fundamental question, we have determined the crystal structure of an avian CD1 (chCD1–2) that shares common ancestry with mammalian CD1 from ≈310 million years ago. The chCD1–2 antigen-binding site consists of a compact, narrow, central hydrophobic groove or pore rather than the more open, 2-pocket architecture observed in mammalian CD1s. Potential antigens then would be restricted in size to single-chain lipids or glycolipids. An endogenous ligand, possibly palmitic acid, serves to illuminate the mode and mechanism of ligand interaction with chCD1–2. The palmitate alkyl chain is inserted into the relatively shallow hydrophobic pore; its carboxyl group emerges at the receptor surface and is stabilized by electrostatic and hydrogen bond interactions with an arginine residue that is conserved in all known CD1 proteins. In addition, other novel features, such as an A′ loop that interrupts and segments the normally long, continuous α1 helix, are unique to chCD1–2 and contribute to the unusually narrow binding groove, thereby limiting its size. Because birds and mammals share a common ancestor, but the rate of evolution is slower in birds than in mammals, the chCD1–2-binding groove probably represents a more primordial CD1-binding groove.

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Graf, Josef A., Reto J. Strasser, and Ulrich Kull. "Structure-Function-Relationship in Thylakoids Influenced by the Pyridazinone BAS 13–338 (SAN 9785)." Zeitschrift für Naturforschung C 42, no. 6 (1987): 808–12. http://dx.doi.org/10.1515/znc-1987-0628.

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The pyridazinone BAS 13-338 (SAN 9785) inhibits the desaturation sequence leading to polyunsaturated fatty acids, mainly of glycolipids. Parallel to the inhibition of fatty acid desaturation in the presence of the pyridazinone, changes in energy-distribution parameters have been observed. These data indicate that the amount of polyunsaturated fatty acids in glycolipids is strongly correlated with excitation, trapping, grouping and dissipation, but not with spillover. Functional changes in energy distribution induced by BAS 13-338 are interpreted as a consequence of structural changes in the lipid matrix, which may imply a structure-function relationship between pigment protein complexes and the surrounding lipid environment in thylakoids.

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Graf, Josef A., Reto J. Strasser, and Ulrich Kuli. "Structure-Function-Relationship in Thylakoids Influenced by the Pyridazinone BAS 13—338 (SAN 9785)." Zeitschrift für Naturforschung C 42, no. 7-8 (1987): 808–12. http://dx.doi.org/10.1515/znc-1987-7-811.

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The pyridazinone BAS 13-338 (SAN 9785|) inhibits the desaturation sequence leading to polyunsaturated fatty acids, mainly of glycolipids. Parallel to the inhibition of fatty acid desaturation in the presence of the pyridazinone, changes in energy-distribution parameters have been observed. These data indicate that the amount of polyunsaturated fatty acids in glycolipids is strongly correlated with excitation, trapping, grouping and dissipation, but not with spillover. Functional changes in energy distribution induced by BAS 13-338 are interpreted as a consequence of structural changes in the lipid matrix, which may imply a structure-function relationship between pigment protein complexes and the surrounding lipid environment in thylakoids.

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Elsaidi, Hassan R. H., and Todd L. Lowary. "Effect of phenolic glycolipids from Mycobacterium kansasii on proinflammatory cytokine release. A structure–activity relationship study." Chemical Science 6, no. 5 (2015): 3161–72. http://dx.doi.org/10.1039/c4sc04004j.

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Jung, Karl-Heinz, and Richard R. Schmidt. "Structure and synthesis of biologically active glycopeptides and glycolipids." Current Opinion in Structural Biology 1, no. 5 (1991): 721–31. http://dx.doi.org/10.1016/0959-440x(91)90171-o.

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Holo, Helge, Margrethe Broch-Due, and John G. Ormerod. "Glycolipids and the structure of chlorosomes in green bacteria." Archives of Microbiology 143, no. 1 (1985): 94–99. http://dx.doi.org/10.1007/bf00414775.

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Kegel, Laurel L., Lajos Z. Szabó, Robin Polt, and Jeanne E. Pemberton. "Alkyl melibioside and alkyl cellobioside surfactants: effect of sugar headgroup and alkyl chain length on performance." Green Chemistry 18, no. 16 (2016): 4446–60. http://dx.doi.org/10.1039/c6gc00436a.

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The potential of glycolipid surfactants, composed of a sugar headgroup and lipid tail, as highly biodegradable and less toxic alternatives to commonly used surfactants motivates the systematic study of structure–function relationships of various glycolipid surfactants.

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Kabayama, Kazuya. "Function and Structure Analysis of Glycolipid Microdomains." Trends in Glycoscience and Glycotechnology 30, no. 174 (2018): E47—E53. http://dx.doi.org/10.4052/tigg.1413.2e.

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Kabayama, Kazuya. "Function and Structure Analysis of Glycolipid Microdomains." Trends in Glycoscience and Glycotechnology 30, no. 174 (2018): J25—J30. http://dx.doi.org/10.4052/tigg.1413.2j.

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Kabayama, Kazuya. "Function and Structure Analysis of Glycolipid Microdomains." Trends in Glycoscience and Glycotechnology 31, no. 181 (2019): SE78—SE79. http://dx.doi.org/10.4052/tigg.1937.2se.

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Kabayama, Kazuya. "Function and Structure Analysis of Glycolipid Microdomains." Trends in Glycoscience and Glycotechnology 31, no. 181 (2019): SJ78—SJ79. http://dx.doi.org/10.4052/tigg.1937.2sj.

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Fischer, Werner, Tibor Mannsfeld, and Gerhard Hagen. "On the basic structure of poly (glycerophosphate) lipoteichoic acids." Biochemistry and Cell Biology 68, no. 1 (1990): 33–43. http://dx.doi.org/10.1139/o90-005.

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Poly(glycerophosphate) lipoteichoic acids from 24 Gram-positive bacteria of the genera Bacillus, Enterococcus, Lactobacillus, Lactococcus, Listeria, Staphylococcus, and the streptococcal pyogenic and oral group were analyzed. The 1,3-linked poly(glycerophosphate) structure was proved by analysis of glycerol and glycerophosphates after acid and alkaline hydrolysis. Using the molar ratios of glycolipid to phosphorus (A) and phosphomonoester to phosphorus after periodate oxidation followed by hydrazinolysis (B) or β-elimination (C), we show that all lipoteichoic acids contain a single unbranched poly(glycerophosphate) chain and that the chain is uniformly phosphodiester-linked to C-6 of the nonreducing hexopyranosyl residue of the glycolipid moiety. On some chains minor phosphate-containing substituents were detected whose structure remains to be clarified. The lipoteichoic acids of enterococci and listeria strains were separated by hydrophobic interaction chromatography into glycolipid- and phosphatidylglycolipid-containing molecular species. The phosphatidylglycolipid moieties were structurally characterized after liberation from lipoteichoic acids with moist acetic acid. After periodate oxidation of lipoteichoic acids β-elimination released both phosphatidic acid and the poly(glycerophosphate) chain. This indicates together with the sequence analysis of the released phosphatidylglycolipid that the phosphatidyl residue is located at C-6 of the reducing hexosyl residue of the glycolipid moiety and the poly(glycerophosphate) chain at C-6 of the nonreducing one. Together with earlier observations these results complete the evidence for the structural and possibly biosynthetic relationship between lipoteichoic acids and glycerophosphoglycolipids.Key words: lipoteichoic acids, poly(glycerophosphate) lipoteichoic acids, Gram-positive bacteria, bacterial membrane.

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Javadi, Ali, Mohamad Reza Pourmand, Javad Hamedi, et al. "Evaluation of anti-biofilm potential of biosurfactant extracted from Nocardia species." Folia Medica 63, no. 3 (2021): 392–99. http://dx.doi.org/10.3897/folmed.63.e54386.

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Introduction: Bacterial natural products such as biosurfactants and surface-active agents are important compounds which exhibit many applications in the &#64257;elds of medicine. Aim: The aim of the present study was to isolate and identify Nocardia strains with high biosurfactant production and antibiofilm ability. Materials and methods: In the present study, a biosurfactant producing Nocardia species was isolated and identi&#64257;ed by a laboratory method. Nocardia species were initially screened and then tested for their ability to produce biosurfactant. The oil spreading test and the surface tension measurements showed that one strain was a biosurfactant producer. The strain with the best surface activity results was selected for further studies and identified by 16S rRNA gene sequencing method. Fourier transform infrared spectroscopy (FTIR) and compositional analysis proved a biosurfactant structure. Results: Oil spreading test and blue agar plate test confirmed biosurfactants and extracellular anionic glycolipids. E24% assay using olive oil revealed strong emulsifying characteristic of the extracted biosurfactant with 100% emulsifying strength. FTIR spectrum indicated the presence of aliphatic hydrocarbon chain (lipid) along with the polysaccharide portion, confirming the glycolipid nature of the biosurfactant. The stability of the biosurfactant produced in different conditions was significant. Increasing concentration of BS significantly inhibited Pseudomonas aeruginosa biofilm. Conclusions: N. coubleae can be a representative of the genus Nocardia for the production of biosurfactants with beneficial physicochemical properties.

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Kim, Jin-Sik, Li Jiao, Jeong-Il Oh, Nam-Chul Ha, and Yong-Hak Kim. "Crystal structure and functional implications of LprF fromMycobacterium tuberculosisandM. bovis." Acta Crystallographica Section D Biological Crystallography 70, no. 10 (2014): 2619–30. http://dx.doi.org/10.1107/s1399004714016599.

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The Gram-positive bacteriaMycobacterium tuberculosisandM. bovisare causative agents of tuberculosis in humans and cattle. The lipoprotein LprF is found inM. tuberculosisandM. bovisbut not in the nonpathogenicM. smegmatis. To date, the role of LprF remains to be elucidated. In this study, the crystal structure of LprF has been determined at 1.1 Å resolution. The overall structure is similar to that of a homologue, LprG, with a central hydrophobic cavity that binds a triacylated glycolipid. LprF exhibited a central cavity structure similar to that of LprG, but with a smaller cavity that binds two alkyl chains. Consistently, subsequent mass-spectrometric analysis revealed that the bound ligand was a diacylated glycolipid, as found in the structure. Furthermore, an increased ratio of lipoarabinomannan to lipomannan in the mycobacterial cell wall was observed whenlprFwas introduced intoM. smegmatis. These observations suggested that LprF transfers the diacylated glycolipid from the plasma membrane to the cell wall, which might be related to the pathogenesis of the bacteria.

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Mayor, S., A. K. Menon, and G. A. Cross. "Glycolipid precursors for the membrane anchor of Trypanosoma brucei variant surface glycoproteins. II. Lipid structures of phosphatidylinositol-specific phospholipase C sensitive and resistant glycolipids." Journal of Biological Chemistry 265, no. 11 (1990): 6174–81. http://dx.doi.org/10.1016/s0021-9258(19)39307-x.

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Mayor, S., A. K. Menon, G. A. Cross, M. A. Ferguson, R. A. Dwek, and T. W. Rademacher. "Glycolipid precursors for the membrane anchor of Trypanosoma brucei variant surface glycoproteins. I. Can structure of the phosphatidylinositol-specific phospholipase C sensitive and resistant glycolipids." Journal of Biological Chemistry 265, no. 11 (1990): 6164–73. http://dx.doi.org/10.1016/s0021-9258(19)39306-8.

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Kanie, Osamu, and Ole Hindsgaul. "Synthesis of oligosaccharides, glycolipids and glycopeptides." Current Opinion in Structural Biology 2, no. 5 (1992): 674–81. http://dx.doi.org/10.1016/0959-440x(92)90200-q.

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