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Journal articles on the topic 'N-Glycosyl Amides'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 February 2022

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1

Gaitonde, Vishwanath, та Steven J. Sucheck. "Synthesis of β-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides". Journal of Carbohydrate Chemistry 31, № 4-6 (2012): 353–70. http://dx.doi.org/10.1080/07328303.2012.663431.

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2

Kunz, Horst, and Norbert Pleuss. "N-Glycosyl Amides as Glycosyl Donors in Stereoselective Glycosylation Reactions." Synthesis 2005, no. 01 (2004): 122–30. http://dx.doi.org/10.1055/s-2004-834911.

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3

Gaitonde, Vishwanath, та Steven J. Sucheck. "ChemInform Abstract: Synthesis of β-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides." ChemInform 43, № 48 (2012): no. http://dx.doi.org/10.1002/chin.201248199.

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4

Talan, Rommel S., Aditya K. Sanki, and Steven J. Sucheck. "Facile synthesis of N-glycosyl amides using a N-glycosyl-2,4-dinitrobenzenesulfonamide and thioacids." Carbohydrate Research 344, no. 15 (2009): 2048–50. http://dx.doi.org/10.1016/j.carres.2009.07.002.

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5

Pleuss, Norbert, and Horst Kunz. "N-Glycosyl Amides: Removal of the Anomeric Protecting Group and Conversion into Glycosyl Donors." Angewandte Chemie International Edition 42, no. 27 (2003): 3174–76. http://dx.doi.org/10.1002/anie.200351351.

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6

Gyóllai, Viktor, László Somsák та László Szilágyi. "N-(1-cyano-d-glycosyl)amides — Novel anomeric α-amino-acid derivatives". Tetrahedron Letters 40, № 20 (1999): 3969–72. http://dx.doi.org/10.1016/s0040-4039(99)00623-1.

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7

Pöhner, Claudia, Vera Ullmann, Ramona Hilpert, Eric Samain та Carlo Unverzagt. "Chemoselective coupling of sugar oximes and α-ketoacids to glycosyl amides and N-glycopeptides". Tetrahedron Letters 55, № 14 (2014): 2197–200. http://dx.doi.org/10.1016/j.tetlet.2014.02.056.

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8

Hollingsworth, Rawle, та Xuezheng Song. "A Stereoselective Synthesis of N-β-d-Glycosyl Amides by a Ritter-type Reaction". Synlett 2006, № 20 (2006): 3451–54. http://dx.doi.org/10.1055/s-2006-958417.

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9

Gyollai, Viktor, Laszlo Somsak та Laszlo Szilagyi. "ChemInform Abstract: N-(1-Cyano-D-glycosyl)amides - Novel Anomeric α-Amino-Acid Derivatives." ChemInform 30, № 35 (2010): no. http://dx.doi.org/10.1002/chin.199935235.

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10

Chennamadhavuni, Divya, та Amy R. Howell. "A solvent-free approach to glycosyl amides: toward the synthesis of α- N -galactosyl ceramides". Tetrahedron Letters 56, № 23 (2015): 3583–86. http://dx.doi.org/10.1016/j.tetlet.2015.02.133.

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11

Kobayashi, Yusuke, Yuya Nakatsuji, Shanji Li, Seiji Tsuzuki, and Yoshiji Takemoto. "Direct N -Glycofunctionalization of Amides with Glycosyl Trichloroacetimidate by Thiourea/Halogen Bond Donor Co-Catalysis." Angewandte Chemie International Edition 57, no. 14 (2018): 3646–50. http://dx.doi.org/10.1002/anie.201712726.

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12

Kobayashi, Yusuke, Yuya Nakatsuji, Shanji Li, Seiji Tsuzuki, and Yoshiji Takemoto. "Direct N -Glycofunctionalization of Amides with Glycosyl Trichloroacetimidate by Thiourea/Halogen Bond Donor Co-Catalysis." Angewandte Chemie 130, no. 14 (2018): 3708–12. http://dx.doi.org/10.1002/ange.201712726.

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13

Poehner, Claudia, Vera Ullmann, Ramona Hilpert, Eric Samain та Carlo Unverzagt. "ChemInform Abstract: Chemoselective Coupling of Sugar Oximes and α-Ketoacids to Glycosyl Amides and N-Glycopeptides." ChemInform 45, № 37 (2014): no. http://dx.doi.org/10.1002/chin.201437214.

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14

Chennamadhavuni, Divya, та Amy R. Howell. "ChemInform Abstract: A Solvent-Free Approach to Glycosyl Amides: Toward the Synthesis of α-N-Galactosyl Ceramides." ChemInform 46, № 40 (2015): no. http://dx.doi.org/10.1002/chin.201540213.

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15

Ferro, Vito, Larry Weiler, Stephen G. Withers, and Herman Ziltener. "Article." Canadian Journal of Chemistry 76, no. 3 (1998): 313–18. http://dx.doi.org/10.1139/v98-018.

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The synthesis of N-glycosyl phosphonamidates has been accomplished via the coupling of peracetylated glycosylamines with an appropriate phosphonochloridate in the presence of pyridine. The resulting glycosyl phosphonamidate esters are dealkylated with bromotrimethylsilane and then deacetylated to give the target compounds, which are potential transition-state analogue inhibitors of glycopeptidases and may prove useful as haptens for generating catalytic antibodies with glycopeptidase activity.Key words: enzyme inhibition, PNGase, phosphonamidate, amide hydrolysis.

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16

Zhang, Hong, Yali Wang, René Thürmer, et al. "Neighbouring Group Participation of C-6 Substituents of Glucose Derivatives on the Stereoselectivity of the N-Glycosidic Linkage of Glycopeptides." Zeitschrift für Naturforschung B 54, no. 5 (1999): 692–98. http://dx.doi.org/10.1515/znb-1999-0519.

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The first example of a glycopeptide with a direct N-α-glycosidic linkage between the trisaccharide and the amino acid residue was found in the glomerular basement membrane of rats. In connection with the total synthesis of nephritogenoside, glycosyl azides with different protecting groups and carbohydrate chain lengths are synthesized, reduced to the corresponding glycosyl amines and coupled with Z-Asp-OBzl. Remarkable differences in the α:β ratio of the condensation products are observed, caused by neighbouring group participation.

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17

Misra, Anup Kumar, Arin Gucchait, and Sritin Ghosh. "Synthesis of Novel Glycosyl Carbamo(dithioperoxo)thioate Derivatives." Synthesis 52, no. 10 (2020): 1523–30. http://dx.doi.org/10.1055/s-0037-1610754.

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A straightforward, one-pot reaction procedure is developed for the synthesis of novel glycosylated carbamo(dithioperoxo)thioate derivatives via N-iodosuccinimide (NIS)-mediated condensation of different glycosyl thiols, carbon disulfide (CS2) and various amines. The reactions occur rapidly and afford good to high yields of the corresponding products.

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18

Norris, Peter. "Pyranose N-Glycosyl Amines: Emerging Targets With Diverse Biological Potential." Current Topics in Medicinal Chemistry 8, no. 2 (2008): 101–13. http://dx.doi.org/10.2174/156802608783378837.

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19

Hager, Christian, Ralf Miethchen, and Helmut Reinke. "Epimerisation of Carbohydrates and Cyclitols, 17.1 Synthesis of Glycosyl Azides and N-Acetyl Glycosyl Amines of Rare Monosaccharides." Synthesis 2000, no. 02 (2000): 226–32. http://dx.doi.org/10.1055/s-2000-6250.

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20

Tanaka, Hiroshi, Yuki Iwata, Daisuke Takahashi, Masaatsu Adachi та Takashi Takahashi. "Efficient Stereoselective Synthesis of γ-N-Glycosyl Asparagines by N-Glycosylation of Primary Amide Groups". Journal of the American Chemical Society 127, № 6 (2005): 1630–31. http://dx.doi.org/10.1021/ja0450298.

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21

Hanessian, Stephen, Dongxu Qiu, Hubli Prabhanjan, Gurijala V. Reddy та Boliang Lou. "Synthesis of clustered D-GalNAc (Tn) and D-Galβ(1→3)GalNAc (T) antigenic motifs using a pentaerythritol scaffold". Canadian Journal of Chemistry 74, № 9 (1996): 1738–47. http://dx.doi.org/10.1139/v96-192.

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The tris(aminoethyl) and triamino derivatives of pentaerythritol have been used as scaffolds or templates for the attachment of immunologically relevant carbohydrates such as D-Galβ(1→3)GalNAc (T) and GalNAc (Tn), through amide linkages with the respective α-glycolyl and α-N-acetyl-L-serinyl glycosides. These clustered glycosidic motifs are intended as haptens for use in the preparation of tumor specific carbohydrate antigens and vaccines. Key words: glycoside synthesis, 2-thiopyridyl carbonate, glycosyl donors and glycopeptide motifs

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22

Li, Shanji, Yusuke Kobayashi та Yoshiji Takemoto. "Organocatalytic Direct α-Selective N-Glycosylation of Amide with Glycosyl Trichloroacetimidate". Chemical and Pharmaceutical Bulletin 66, № 7 (2018): 768–70. http://dx.doi.org/10.1248/cpb.c18-00255.

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23

Hager, Christian, Ralf Miethchen, and Helmut Reinke. "ChemInform Abstract: Epimerization of Carbohydrates and Cyclitols. Part 17. Synthesis of Glycosyl Azides and N-Acetyl Glycosyl Amines of Rare Monosaccharides." ChemInform 31, no. 21 (2010): no. http://dx.doi.org/10.1002/chin.200021206.

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24

FRISON, Natacha, Philippe MARCEAU, Annie-Claude ROCHE, Michel MONSIGNY, and Roger MAYER. "Oligolysine-based saccharide clusters: synthesis and specificity." Biochemical Journal 368, no. 1 (2002): 111–19. http://dx.doi.org/10.1042/bj20020673.

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In search of specific and highly selective sugar clusters for cell receptors, such as membrane lectins, various disaccharides were coupled to small peptide cores through an amide bond. In a first step, the reducing disaccharides, i.e. lactose and three different dimannoses, were converted into glycosyl-pyroglutamyl-β-alanine derivatives. The free carboxylic group of these conjugates was then coupled to the α and ∊ amino groups of the core peptide (Lysn-Ala-Cys-NH2) with n = 1 to 5, with complete substitution leading to homogeneous glycoclusters. The thiol group of the cysteine residue was used

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25

MICHALSKA, M., W. KUDELSKA, J. PLUSKOWSKI, M. NOWINSKA та A. JUSZCZAK. "ChemInform Abstract: A Highly Stereoselective Synthesis of N-Alkyl(2-deoxy-β-D-arabino- hexopyranosyl)amines via 2-Deoxyglycosyl Phosphorodithioates as Glycosyl Donors." ChemInform 25, № 31 (2010): no. http://dx.doi.org/10.1002/chin.199431245.

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26

Das, T. Mohan, Chebrolu P. Rao, and Erkki Kolehmainen. "Synthesis and characterisation of N-glycosyl amines from the reaction between 4,6-O-benzylidene-d-glucopyranose and substituted aromatic amines and also between 2-(o-aminophenyl)benzimidazole and pentoses or hexoses." Carbohydrate Research 334, no. 4 (2001): 261–69. http://dx.doi.org/10.1016/s0008-6215(01)00202-6.

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27

Pingel, S., and M. Duszenko. "Identification of two distinct galactosyltransferase activities acting on the variant surface glycoprotein of Trypanosoma brucei." Biochemical Journal 283, no. 2 (1992): 479–85. http://dx.doi.org/10.1042/bj2830479.

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Variant surface glycoproteins (VSGs) of Trypanosoma brucei contain two distinct glycosylation sites: (1) N-linked glycans within the protein portion of the molecules, and (2) the glycosyl-phosphatidylinositol (GPI) membrane anchor. Since galactose residues show uncommon alpha-glycosidic linkages in the GPI membrane anchor, we were prompted to investigate galactosylation of the GPI anchor. On comparing a trypanosome clone galactosylated exclusively in N-glycans (clone MITat 1.5) with clones galactosylated predominantly in the glypiated membrane anchor (clones MITat 1.4, MITat 1.6 and AnTat 1.8)

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28

Crump, Elizabeth M., Malcolm B. Perry, Sharon C. Clouthier, and William W. Kay. "Antigenic Characterization of the Fish Pathogen Flavobacterium psychrophilum." Applied and Environmental Microbiology 67, no. 2 (2001): 750–59. http://dx.doi.org/10.1128/aem.67.2.750-759.2001.

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ABSTRACT Flavobacteria are a poorly understood and speciated group of commensal bacteria and opportunistic pathogens. The psychrotrophFlavobacterium psychrophilum is the etiological agent of rainbow trout fry syndrome and bacterial cold water disease, septicemic diseases that heavily impact salmonids. Consequently, two verified but geographically diverse isolates were characterized phenotypically and biochemically. A facile typing system was devised which readily discriminated between closely related species and was verified against a pool of recent prospective isolates. F. psychrophilum was f

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29

Das, T. Mohan, Chebrolu P. Rao, and Erkki Kolehmainen. "ChemInform Abstract: Synthesis and Characterization of N-Glycosyl Amines from the Reaction Between 4,6-O-Benzylidene-D-glucopyranose and Substituted Aromatic Amines and also Between 2-(o-Aminophenyl)benzimidazole and Pentoses or Hexoses." ChemInform 33, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.200203207.

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30

Pleuss, Norbert, and Horst Kunz. "N-Glycosyl Amides as Glycosyl Donors in Stereoselective Glycosylation Reactions." ChemInform 36, no. 21 (2005). http://dx.doi.org/10.1002/chin.200521205.

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31

Pleuss, Norbert, and Horst Kunz. "N-Glycosyl Amides: Removal of the Anomeric Protecting Group and Conversion into Glycosyl Donors." ChemInform 34, no. 44 (2003). http://dx.doi.org/10.1002/chin.200344186.

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32

Mała, Patrycja, та Christian Marcus Pedersen. "Self‐Promoted Glycosylation for the Synthesis of β‐ N ‐Glycosyl Sulfonyl Amides". European Journal of Organic Chemistry, 27 серпня 2021. http://dx.doi.org/10.1002/ejoc.202100808.

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33

Song, Xuezheng, та Rawle I. Hollingsworth. "A Stereoselective Synthesis of N-β-D-Glycosyl Amides by a Ritter-Type Reaction." ChemInform 38, № 16 (2007). http://dx.doi.org/10.1002/chin.200716189.

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34

Tanaka, Hiroshi, Yuki Iwata, Daisuke Takahashi, Masaatsu Adachi та Takashi Takahashi. "Efficient Stereoselective Synthesis of γ-N-Glycosyl Asparagines by N-Glycosylation of Primary Amide Groups." ChemInform 36, № 26 (2005). http://dx.doi.org/10.1002/chin.200526126.

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