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Journal articles on the topic '2-Deoxy Oligosaccharides'

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Published: 4 June 2021

Last updated: 6 September 2023

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1

Kazakova, Ekaterina D., Dmitry V. Yashunsky, Elena A. Khatuntseva, and Nikolay E. Nifantiev. "Azidophenylselenylation of glycals towards 2-azido-2-deoxy-selenoglycosides and their application in oligosaccharide synthesis." Pure and Applied Chemistry 92, no. 7 (2020): 1047–56. http://dx.doi.org/10.1515/pac-2020-0105.

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Abstract2-Amino-2-deoxy-pyranosyl units are important structural components of cell-wall polymers in prokaryotes, fungi and mammals. With respect to the need for development of novel and efficient vaccines and tools for serodiagnosis of infectious diseases, of particular interest are the oligosaccharide cell-wall antigens of pathogenic bacteria and fungi, which comprise 2-amino-2-deoxy-D-glucopyranose and 2-amino-2-deoxy-D-galactopyranose units as α- or β-anomers. Synthesis of N-acylated α-GlcN and α-GalN containing oligosaccharides is a special challenge due to the presence of a participating

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2

Cai, Zhi Peng, Wen Li Wang, Louis Conway, et al. "1,3-Di(2-dipyridyl)propan-1,3-dione – a new fluorogenic labeling reagent for milk oligosaccharides." Pure and Applied Chemistry 89, no. 7 (2017): 921–29. http://dx.doi.org/10.1515/pac-2016-0914.

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Abstract:We herein demonstrate the use of 1,3-di(2-dipyridyl)propan-1,3-dione (DPPD) as a fluorogenic label for oligosaccharides. A number of milk-derived oligosaccharide standards were successfully labeled with this reagent, with the advantage of greatly simplified sample preparation compared to other commonly used fluorescent tags. DPPD shows a selectivity for oligosaccharides which do not possess a 2-acetamido-2-deoxy-hexose moiety at the reducing terminus, potentially aiding in the identification of complex mixtures of carbohydrates. The use of DPPD for the structural determination of olig

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3

Schwartz, David A., Ho-Huat Lee, Jeremy P. Carver, and Jiri J. Krepinsky. "Syntheses of model oligosaccharides of biological significance. 4. Synthesis of a fucosylated N,N′-diacetylchitobioside and related oligosaccharides." Canadian Journal of Chemistry 63, no. 5 (1985): 1073–79. http://dx.doi.org/10.1139/v85-182.

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The synthesis of two trisaccharides and one disaccharide containing L-fucose and 2-acetamido-2-deoxy-D-glucose is reported. Methyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside was glycosylated with a 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide. Removal of the phthalimido protecting groups by hydrazinolysis followed by N-acetylation and debenzylation yielded methyl N,N′-diacetylchitobioside 3′,4′,6′-triacetate. The latter was selectively fucosylated at the 6-position with 2,3,4-tri-O-benzyl-α-L-fucopyranosyl bromide to yield, after debenzylation and de-O-ace

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4

Bongat, Aileen F. G., Medha N. Kamat, and Alexei V. Demchenko. "Chemoselective Synthesis of Oligosaccharides of 2-Deoxy-2-aminosugars." Journal of Organic Chemistry 72, no. 4 (2007): 1480–83. http://dx.doi.org/10.1021/jo062171d.

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5

Banoub, Joseph, Paul Boullanger, and Dominique Lafont. "Synthesis of oligosaccharides of 2-amino-2-deoxy sugars." Chemical Reviews 92, no. 6 (1992): 1167–95. http://dx.doi.org/10.1021/cr00014a002.

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6

Pongdee, Rongson, Bin Wu та Gary A. Sulikowski. "One-Pot Synthesis of 2-Deoxy-β-oligosaccharides". Organic Letters 3, № 22 (2001): 3523–25. http://dx.doi.org/10.1021/ol016593f.

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7

Hanna, H. Rizk, та David R. Bundle. "Antibody–oligosaccharide interactions: the synthesis of 2-deoxy-α-L-rhamnose containing oligosaccharide haptens related to Shigella flexneri variant Y antigen". Canadian Journal of Chemistry 71, № 1 (1993): 125–34. http://dx.doi.org/10.1139/v93-018.

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A series of di- and trisaccharide glycosides based on the α-L-Rha(1 → 3)β-D-GlcNAc and α-L-Rha(1 → 3)α-L-Rha(1 → 3)β-D-GlcNAc elements have been synthesized to locate the minimal oligosaccharide determinant of the Shigella flexneri O-polysaccharide, which is built from a tetrasaccharide repeating unit, [ → 2) α-L-Rhap(1 → 2)α-L-Rhap(1 → 3)α-L-Rhap(1 → 3)β-D-GlcNAcp(1-]n. These compounds also serve to identify the carbohydrate surface of the Shigella antigen that interacts with a monoclonal antibody, currently the subject of crystallographic studies. Two strategies utilizing suitably protected

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8

Rodríguez, Miguel Ángel, Omar Boutureira, Xavier Arnés, M. Isabel Matheu, Yolanda Díaz, and Sergio Castillón. "Stereoselective Synthesis of 2-Deoxy-2-iodo-glycosides from Furanoses. A New Route to 2-Deoxy-glycosides and 2-Deoxy-oligosaccharides ofriboandxyloConfiguration." Journal of Organic Chemistry 70, no. 25 (2005): 10297–310. http://dx.doi.org/10.1021/jo051461b.

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9

Whitfield, Dennis M., Henrianna Pang, Jeremy P. Carver та Jiri J. Krepinsky. "Syntheses of model oligosaccharides of biological significance. X.•Syntheses and NMR and mass spectral analysis of trideuteriomethyl di-3,6-O-(4-O-β-D-galactopyranosyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside: the I antigen branchpoint penta- and tetrasaccharides and a related trisaccharide". Canadian Journal of Chemistry 68, № 6 (1990): 942–52. http://dx.doi.org/10.1139/v90-147.

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As part of our studies of complex oligosaccharides, in particular their three-dimensional structure, we have synthesized the antigen I branchpoint penta- and tetrasaccharides. The unbranched trisaccharide 3D was also synthesized, and its derivative 3B served as the intermediate for the synthesis of higher oligosaccharides. NMR spectra of major intermediates as well as of the final oligosaccharides were completely assigned. Mass spectra of the synthetic intermediates and the final oligosaccharides were analyzed and compared with those of a similar group of oligosaccharides containing L-fucose,

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10

BANOUB, J., P. BOULLANGER, and D. LAFONT. "ChemInform Abstract: Synthesis of Oligosaccharides of 2-Amino-2-deoxy Sugars." ChemInform 24, no. 12 (2010): no. http://dx.doi.org/10.1002/chin.199312317.

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11

Dickenson, J. M., T. N. Huckerby та I. A. Nieduszynski. "Skeletal keratan sulphate chains isolated from bovine intervertebral disc may terminate in α(2----6)-linked N-acetylneuraminic acid". Biochemical Journal 282, № 1 (1992): 267–71. http://dx.doi.org/10.1042/bj2820267.

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Peptido-keratan sulphate fragments were isolated from the nucleus pulposus of bovine intervertebral discs (2-year-old animals) after digestion with chondroitin ABC lyase followed by digestion with diphenylcarbamoyl chloride-treated trypsin of A1D1 proteoglycans and gel-permeation chromatography on Sepharose CL-6B. The peptido-keratan sulphate fragments were subjected to alkaline borohydride reduction. The reduced chains were treated with keratanase in the presence of the sialidase inhibitor 2,3-dehydro-2-deoxy-N-acetylneuraminic acid, and the digest was subjected to alkaline borohydride reduct

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12

Pongdee, Rongson, Bin Wu та Gary A. Sulikowski. "ChemInform Abstract: One-Pot Synthesis of 2-Deoxy-β-oligosaccharides." ChemInform 33, № 9 (2010): no. http://dx.doi.org/10.1002/chin.200209206.

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13

Díaz, Yolanda, Sergio Castillón, and Xavier Arnés. "Phenyl 2-Deoxy-2-iodo-1-thio-glycosides: New Glycosyl Donors for the Stereoselective Synthesis of 2-Deoxy-oligosaccharides." Synlett, no. 14 (2003): 2143–46. http://dx.doi.org/10.1055/s-2003-42066.

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14

Gainsford, Graeme J., Ralf Schwörer, Peter C. Tyler, and Olga V. Zubkova. "Crystal packing in three related disaccharides: precursors to heparan sulfate oligosaccharides." Acta Crystallographica Section E Crystallographic Communications 71, no. 6 (2015): 582–87. http://dx.doi.org/10.1107/s2056989015008518.

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The three title compounds form part of a set of important precursor dissacharides which lead to novel therapeutics, in particular for Alzheimer's disease. All three crystallize as poorly diffracting crystals with one independent molecule in the asymmetric unit. Two of them are isostructural: 4-methoxyphenyl 4-O-[6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(9-fluorenylmethyloxycarbonyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-chloroacetyl-α-L-idopyranoside, C59H56ClN3O16, (I), theido-relative of a reportedgluco-disaccharide [Gainsfordet al., 2013).Acta Cryst.C69, 679–682] and 4-methoxyphen

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15

Fujiwara, Nagatoshi, Noboru Nakata, Takashi Naka, et al. "Structural Analysis and Biosynthesis Gene Cluster of an Antigenic Glycopeptidolipid from Mycobacterium intracellulare." Journal of Bacteriology 190, no. 10 (2008): 3613–21. http://dx.doi.org/10.1128/jb.01850-07.

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ABSTRACT Mycobacterium avium-Mycobacterium intracellulare complex (MAC) is the most common isolate of nontuberculous mycobacteria and causes pulmonary and extrapulmonary diseases. MAC species can be grouped into 31 serotypes by the epitopic oligosaccharide structure of the species-specific glycopeptidolipid (GPL) antigen. The GPL consists of a serotype-common fatty acyl peptide core with 3,4-di-O-methyl-rhamnose at the terminal alaninol and a 6-deoxy-talose at the allo-threonine and serotype-specific oligosaccharides extending from the 6-deoxy-talose. Although the complete structures of 15 ser

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16

Lukasiewicz, Jolanta, Tomasz Niedziela, Wojciech Jachymek, Lennart Kenne, and Czeslaw Lugowski. "Two Kdo-Heptose Regions Identified in Hafnia alvei 32 Lipopolysaccharide: the Complete Core Structure and Serological Screening of Different Hafnia O Serotypes." Journal of Bacteriology 191, no. 2 (2008): 533–44. http://dx.doi.org/10.1128/jb.00891-08.

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ABSTRACT Hafnia alvei, a gram-negative bacterium, is an opportunistic pathogen associated with mixed hospital infections, bacteremia, septicemia, and respiratory diseases. Various 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo)-containing fragments different from known structures of core oligosaccharides were previously found among fractions obtained by mild acid hydrolysis of some H. alvei lipopolysaccharides (LPSs). However, the positions of these segments in the LPS structure were not known. Analysis of de-N,O-acylated LPS by nuclear magnetic resonance spectroscopy and mass spectrometry allowed t

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17

Boutureira, Omar, Miguel A. Rodríguez, David Benito, M. Isabel Matheu, Yolanda Díaz, and Sergio Castillón. "Stereoselective Synthesis of 2-Deoxy-2-phenylselenenyl Glycosides from Furanoses: Implication of the Phenylselenenyl Group in the Stereocontrolled Preparation of 2-Deoxy-ribo- and 2-Deoxy-xylo-oligosaccharides." European Journal of Organic Chemistry 2007, no. 21 (2007): 3564–72. http://dx.doi.org/10.1002/ejoc.200700161.

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18

Blatter, Géraldine, Jean-Marie Beau, and Jean-Claude Jacquinet. "The use of 2-deoxy-2-trichloroacetamido-d-glucopyranose derivatives in syntheses of oligosaccharides." Carbohydrate Research 260, no. 2 (1994): 189–202. http://dx.doi.org/10.1016/0008-6215(94)84038-5.

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19

Paul, Somak, Srinivasarao Raghothama, and Narayanaswamy Jayaraman. "Synthesis of 2-deoxy cyclic and linear oligosaccharides by oligomerization of monomers." Carbohydrate Research 344, no. 2 (2009): 177–86. http://dx.doi.org/10.1016/j.carres.2008.10.026.

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20

Zhang, Jianbo, Youxian Dong, Madina Yuma, et al. "Copper-Catalyzed Stereoselective Synthesis of 2-Deoxygalactosides." Synlett 31, no. 11 (2020): 1087–93. http://dx.doi.org/10.1055/s-0040-1707098.

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An efficient glycosylation method to synthesize 2-deoxy-O-galactosides based on a Cu(II)-catalyzed reaction without additional ligand has been developed. The glycosylation was amenable to different protected glycal donors and a wide range of acceptors including alcohols, amino acids, sugars, and phenol, and proceeds with excellent yield and high α-selectivity under mild conditions. The reaction proceeds readily on a gram scale, and its versatility is exemplified in the synthesis of oligosaccharides.

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21

Peng, Hong, Yong Sun, Junhua Zhang, and Lu Lin. "Degradation of cellooligosaccharides in oxidative medium and alkaline medium: HPLC, FTIR, and GC-MS analyses." BioResources 5, no. 2 (2010): 616–33. http://dx.doi.org/10.15376/biores.5.2.616-633.

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The chemical degradations of highly-purified cellotriose, cellotetraose, and cellopentaose in H2O2 and NaOH media were studied, respectively. The degradation products were analyzed by HPLC, FTIR, and GC-MS techniques. The results show that for the three oligosaccharides the main oxidative degradation products are 2, 3-dihydroxy-butanedioic acid, 2-keto-gluconic acid, glucopyranose, D-glucose, D-gluconic acid, and cellooligosaccharides with lower DP. A small amount of arabinose is formed during the oxidation of cellotriose. The main alkaline degradation products for the three oligomers include

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22

Hada, Noriyasu, Tokio Morita, Takashi Ueda, et al. "Synthesis of the Carbohydrate Moiety of Glycoproteins from the Parasite Echinococcus granulosus and Their Antigenicity against Human Sera." Molecules 26, no. 18 (2021): 5652. http://dx.doi.org/10.3390/molecules26185652.

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Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the carbohydrate moiety of glycoprotein from Echinococcus granulosus have been accomplished. Trisaccharide Galβ1-3Galβ1-3GalNAcα1-R (A), tetrasaccharide Galα1-4Galβ1-3Galβ1-3GalNAcα1-R (B), and pentasaccharide Galα1-4Galβ1-3Galβ1-3Galβ1-3GalNAcα1-R (C), (R = biotinylated probe) were synthesized by stepwise condensation and/or block synthesis by the use of 5-(methoxycarbonyl)pentyl 2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranoside as a common glycosyl acceptor. The synthesis of the tetrasaccharide and the pen

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23

VOCADLO, David J., Lloyd F. MACKENZIE, Shouming HE, Gregory J. ZEIKUS та Stephen G. WITHERS. "Identification of Glu-277 as the catalytic nucleophile of Thermoanaerobacterium saccharolyticum β-xylosidase using electrospray MS". Biochemical Journal 335, № 2 (1998): 449–55. http://dx.doi.org/10.1042/bj3350449.

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Thermoanaerobacterium saccharolyticum β-xylosidase is a member of family 39 of the glycosyl hydrolases. This grouping comprises both retaining β-d-xylosidases and α-l-iduronidases. T. saccharolyticum β-xylosidase catalyses the hydrolysis of short xylo-oligosaccharides into free xylose via a covalent xylosyl–enzyme intermediate. Incubation of T. saccharolyticum β-xylosidase with 2,4-dinitrophenyl 2-deoxy-2-fluoro-β-d-xyloside resulted in time-dependent inactivation of the enzyme (inactivation rate constant ki = 0.089 min-1, dissociation constant for the inactivator Ki = 65 µM) through the accum

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24

Defaye, Jacques, Andrée Gadelle та Christian Pedersen. "A convenient access to β-(1 → 4)-linked 2-amino-2-deoxy-d-glucopyranosyl fluoride oligosaccharides and β-(1 → 4)-linked 2-amino-2-deoxy-d-glucopyranosyl oligosaccharides by fluorolysis and fluorohydrolysis of chitosan". Carbohydrate Research 261, № 2 (1994): 267–77. http://dx.doi.org/10.1016/0008-6215(94)84023-7.

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25

McDowell, W., T. J. Grier, J. R. Rasmussen, and R. T. Schwarz. "The role of C-4-substituted mannose analogues in protein glycosylation. Effect of the guanosine diphosphate esters of 4-deoxy-4-fluoro-d-mannose and 4-deoxy-d-mannose on lipid-linked oligosaccharide assembly." Biochemical Journal 248, no. 2 (1987): 523–31. http://dx.doi.org/10.1042/bj2480523.

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The effects of the guanosine diphosphate esters of 4-deoxy-4-fluoro-D-mannose (GDP-4FMan) and 4-deoxy-D-mannose (GDP-4dMan) on reactions of the dolichol pathway in chick-embryo cell microsomal membranes were investigated by studies with chick-embryo cell microsomal membranes in vitro and in baby-hamster kidney (BHK) cells in vivo. Each nucleotide sugar analogue inhibited lipid-linked oligosaccharide biosynthesis in a concentration-dependent manner. GDP-4FMan blocked in vitro the addition of mannose to Dol-PP-(GlcNAc)2Man from GDP-Man (where Dol represents dolichol), but did not interfere with

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26

Lee, Ho-Huat, David A. Schwartz, John F. Harris, Jeremy P. Carver, and Jiri J. Krepinsky. "Syntheses of model oligosaccharides of biological significance. 7.Synthesis of a fucosylated N,N′-diacetylchitobioside linked to bovine serum albumin and immunochemical characterization of rabbit antisera to this structure." Canadian Journal of Chemistry 64, no. 9 (1986): 1912–18. http://dx.doi.org/10.1139/v86-315.

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Synthesis of methoxycarbonyloctyl 2-acetamido-4-O-[(2′-acetamido-2′-deoxy-β-D-glucopyranosyl)-6-O-α-L-fucopyranosyl]-2-deoxy-(β-D-glucopyranoside as shown in Scheme 1 is described together with coupling it with bovine serum albumin and poly-L-lysine. Mouse and rabbit antisera to the BSA conjugate were prepared and partially characterized.

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27

Lennholm, Helena, Bengt Lindberg, Ulf Lindquist, Frank Lindh, and Bo Nilsson. "N-Deacetylation of 2-acetamido-2-deoxy-hexosecontaining oligosaccharides and polysaccharides by calcium in liquid ammonia." Glycoconjugate Journal 4, no. 4 (1987): 313–16. http://dx.doi.org/10.1007/bf01048364.

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28

Sanderson, P. N., T. N. Huckerby, and I. A. Nieduszynski. "Chondroitinase ABC digestion of dermatan sulphate. N.m.r. spectroscopic characterization of the oligo- and poly-saccharides." Biochemical Journal 257, no. 2 (1989): 347–54. http://dx.doi.org/10.1042/bj2570347.

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Dermatan sulphates, in which iduronate was the predominant uronate constituent, were partially digested by chondroitinase ABC to produce oligosaccharides of the following structure: delta UA-[GalNAc(4SO3)-IdoA]mGalNAc(4SO3) [where m = 0-5, delta UA represents beta-D-gluco-4-enepyranosyluronate, IdoA represents alpha-L-iduronate and GalNAc(4SO3) represents 2-acetamido-2-deoxy-beta-D-galactose 4-O-sulphate], which were fractionated by gel-permeation chromatography and examined by 100 MHz 13C-n.m.r. and 400/500 MHz 1H-n.m.r. spectroscopy. Experimental conditions were established for the removal o

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29

Whitfield, Dennis M., Caroline J. Ruzicka, Jeremy P. Carver та Jiri J. Krepinsky. "Syntheses of model oligosaccharides of biological significance. 9. Syntheses of trideuteriomethyl di-3,6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside: the I antigen branch-point trisaccharide and related disaccharides". Canadian Journal of Chemistry 65, № 4 (1987): 693–703. http://dx.doi.org/10.1139/v87-118.

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The title trisaccharide, 13c, was synthesized, as well as its two component disaccharides, 10c and 11c. Four disaccharides, 3c, 4c, 5c, and 7c, were also prepared to serve as model compounds for the investigation of the 3-dimensional structure of more complex oligosaccharides. The β-1,3 linkage was formed in 75% yield by coupling 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (9) with trideuteriomethyl 2-O-benzoyl-4,6-benzylidene-β-D-galactopyranoside (2a), using silver trifluoromethanesulphonate as a promoter in the presence of the base 2,6-di-tert-butyl-4-methylpyridine.

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30

Micheli, E. "A new approach to the synthesis of β-glycosidically linked oligosaccharides containing 2-acetamido-2-deoxy-?-mannose residues". Carbohydrate Research 139, № 1 (1985): C1—C3. http://dx.doi.org/10.1016/0008-6215(85)85095-3.

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31

Murase, Takefumi, and Yasuhiro Kajihara. "Unique cleavage of 2-acetamido-2-deoxy-d-glucose from the reducing end of biantennary complex type oligosaccharides." Carbohydrate Research 345, no. 12 (2010): 1702–7. http://dx.doi.org/10.1016/j.carres.2010.05.020.

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32

Kaga, Harumi, Masaru Enomoto, Hiroki Shimizu, et al. "Microwave-Assisted Heating Reactions of N-Acetylglucosamine (GlcNAc) in Sulfolane as a Method Generating 1,6-Anhydrosugars Consisting of Amino Monosaccharide Backbones." Molecules 25, no. 8 (2020): 1944. http://dx.doi.org/10.3390/molecules25081944.

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The microwave-assisted heating reaction of N-acetyl glucosamine (GlcNAc) in sulfolane is described. The reaction produces two major products that are assignable to 1,6-anhydro-2-acetamido-2-deoxy-β-d-glucopyranose (AGPNAc) and 1,6-anhydro-2-acetamido-2-deoxy-β-d-glucofuranose (AGFNAc). In order to reveal a general feature of the system, the 3, 5, and 10 min reactions were performed at 140, 160, 180, 200, and 220 °C to clarify the time course changes in the conversion of GlcNAc and the yields of the two produced 1,6-anhydrosugars. Temperature is a crucial factor that significantly affects the c

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33

DEFAYE, J., A. GADELLE та C. PEDERSEN. "ChemInform Abstract: Carbohydrate Reactivity in Anhydrous Hydrogen Fluoride. Part 17. A Convenient Access to β-(1 → 4)-Linked 2-Amino-2-deoxy-D- glucopyranosyl Fluoride Oligosaccharides and β-(1 → 4)- Linked 2-Amino-2-deoxy-D-glucopyranosyl Oligosaccharid". ChemInform 26, № 2 (2010): no. http://dx.doi.org/10.1002/chin.199502159.

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34

Mischnick, Petra, Britta Evers та Joachim Thiem. "Analysis of oligosaccharides containing 2-deoxy-α-d- arabino-hexosyl residues by the reductive-cleavage method". Carbohydrate Research 264, № 2 (1994): 293–304. http://dx.doi.org/10.1016/s0008-6215(05)80013-8.

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35

Kallin, Elisabeth, Hans L�nn, and Thomas Norberg. "Derivatization procedures for reducing oligosaccharides, part 2: Chemical transformation of 1-deoxy-1-(4-trifluoroacetamidophenyl)aminoalditols." Glycoconjugate Journal 5, no. 2 (1988): 145–50. http://dx.doi.org/10.1007/bf01061203.

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36

Burzyńska, Patrycja, Marlena Jodłowska, Agata Zerka, Jan Czujkowski, and Ewa Jaśkiewicz. "Red Blood Cells Oligosaccharides as Targets for Plasmodium Invasion." Biomolecules 12, no. 11 (2022): 1669. http://dx.doi.org/10.3390/biom12111669.

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The key element in developing a successful malaria treatment is a good understanding of molecular mechanisms engaged in human host infection. It is assumed that oligosaccharides play a significant role in Plasmodium parasites binding to RBCs at different steps of host infection. The formation of a tight junction between EBL merozoite ligands and glycophorin receptors is the crucial interaction in ensuring merozoite entry into RBCs. It was proposed that sialic acid residues of O/N-linked glycans form clusters on a human glycophorins polypeptide chain, which facilitates the binding. Therefore, s

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37

Dasgupta, Falguni, та Laurens Anderson. "1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-d-glucopyranose as a glycosyl donor in syntheses of oligosaccharides". Carbohydrate Research 202 (липень 1990): 239–55. http://dx.doi.org/10.1016/0008-6215(90)84083-7.

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38

Micheli, Emilio, Francesco Nicotra, Luigi Panza, Fiamma Ronchetti та L. Toma. "A new approach to the synthesis of β-glycosidically linked oligosaccharides containing 2-acetamido-2-deoxy-d-mannose residues". Carbohydrate Research 139 (червень 1985): C1—C3. http://dx.doi.org/10.1016/0008-6215(85)90030-8.

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39

Zhang, Jianjun, Shiqiang Yan, Xiaomei Liang, Jingping Wu, Daoquan Wang та Fanzuo Kong. "Practical preparation of 2-azido-2-deoxy-β-d-mannopyranosyl carbonates and their application in the synthesis of oligosaccharides". Carbohydrate Research 342, № 18 (2007): 2810–17. http://dx.doi.org/10.1016/j.carres.2007.09.001.

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Zanetta, J. P., V. Gouyer, E. Maes, et al. "Massive in vitro synthesis of tagged oligosaccharides in 1-benzyl-2-acetamido-2-deoxy- -D-galactopyranoside treated HT-29 cells." Glycobiology 10, no. 6 (2000): 565–75. http://dx.doi.org/10.1093/glycob/10.6.565.

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Beierbeck, Helmut, and Raymond U. Lemieux. "Computer simulation studies of the solvation of oligosaccharides." Canadian Journal of Chemistry 68, no. 6 (1990): 820–27. http://dx.doi.org/10.1139/v90-130.

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Abstract:

Computer simulations of the hydration of the tetrasaccharide αLFuc(1 → 2)βDGal(1 → 3) αLFuc(1 → 4) βDGlcNAc-OMe and one of its deoxy derivatives were carried out as a first step toward an understanding of the role of water in the recognition of oligosaccharides by proteins. The model consisted of one solute molecule in one of its low-energy conformations, surrounded by 250 water molecules. The solute–water and water–water interaction energies were evaluated with Clementi's potentials. Ensemble states for the derivation of average properties were generated by Monte Carlo methods. As expected, t

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David, Serge, Annie Malleron та Christophe Dini. "Preparation of oligosaccharides with β-d-mannopyranosyl and 2-azido-2-deoxy-β-d-mannopyranosyl residues by inversion at C-2 after coupling". Carbohydrate Research 188 (червень 1989): 193–200. http://dx.doi.org/10.1016/0008-6215(89)84070-4.

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Bosso, Claude, Jacques Defaye, Alain Domard, Andrée Gadelle та Christian Pedersen. "The behavior of chitin towards anhydrous hydrogen fluoride. Preparation of β-(1→4)-linked 2-acetamido-2-deoxy-d-glucopyranosyl oligosaccharides". Carbohydrate Research 156 (листопад 1986): 57–68. http://dx.doi.org/10.1016/s0008-6215(00)90099-5.

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ZHU, Zhen-Yuan, Yong-Min ZHANG, Chao SUN, and Yan-Ping YAO. "Synthesis of ProtectedN-Acetylchitooligosaccharide and Its Analogues: A Versatile Approach for the Synthesis of Complex Oligosaccharides of 2-Amino-2-deoxy Sugar." Chinese Journal of Chemistry 26, no. 8 (2008): 1519–22. http://dx.doi.org/10.1002/cjoc.200890275.

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Defaye, Jacques, Andrée Gadelle та Christian Pedersen. "Hydrogen fluoride-catalyzed formation of glycosides. Preparation of methyl 2-acetamido-2-deoxy-β-d-gluco- and -β-d-galacto-pyranosides, and of β-(1→6)-linked 2-acetamido-2-deoxy-d-gluco- and -d-galacto-pyranosyl oligosaccharides". Carbohydrate Research 186, № 2 (1989): 177–88. http://dx.doi.org/10.1016/0008-6215(89)84033-9.

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Shen, Zhengnan, Hani Mobarak, Wei Li, Göran Widmalm та Biao Yu. "Synthesis of β-(1→2)-Linked 6-Deoxy-l-altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of anortho-Hexynylbenzoate Donor". Journal of Organic Chemistry 82, № 6 (2017): 3062–71. http://dx.doi.org/10.1021/acs.joc.7b00057.

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Chen, Jiun-Han, Jyh-Herng Ruei та Kwok-Kong Tony Mong. "Iterative α-Glycosylation Strategy for 2-Deoxy- and 2,6-Dideoxysugars: Application to the One-Pot Synthesis of Deoxysugar-Containing Oligosaccharides". European Journal of Organic Chemistry 2014, № 9 (2014): 1827–31. http://dx.doi.org/10.1002/ejoc.201400006.

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Pradhan, Tapan Kumar, Chun Cheng Lin та Kwok-Kong Tony Mong. "Preparation of a Protected 3-Deoxy-d-manno-oct-2-ulosonate Glycal Donor for the Synthesis of β-KDO-Containing Oligosaccharides". Organic Letters 16, № 5 (2014): 1474–77. http://dx.doi.org/10.1021/ol500275j.

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Lehmann, Jochen, та Stefan Petry. "Spacer-modified oligosaccharides as potential affinity reagents for glycosyltransferases: the preparation and enzymic galactosylation of 1,10-bis(2-acetamido-2-deoxy-β-d-glucopyranosyloxy)decane". Carbohydrate Research 204 (вересень 1990): 141–44. http://dx.doi.org/10.1016/0008-6215(90)84029-t.

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Jain, Rakesh K., Conrad F. Piskorz та Khushi L. Matta. "A convenient synthesis of N-acetyllactosamine-linked oligosaccharides from phenyl 3,6,2′,3′,4′,6′-hexa-O-acetyl- 2-deoxy-2-phthalimido-1-thio-β-lactopyranoside". Carbohydrate Research 243, № 2 (1993): 385–91. http://dx.doi.org/10.1016/0008-6215(93)87042-q.

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