通过非经典卤离子催化立体选择性制备2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖的烷基糖苷以及α-D-半乳糖p-(1→3)-α-D-葡萄糖pNAc-OMe的合成与核磁共振光谱分析 - Suppr

Stereoselective preparation of alkyl glycosides of 2-acetamido-2-deoxy-alpha-D-glucopyranose by nonclassical halide-ion catalysis and synthesis and NMR spectroscopy of alpha-D-Gal p-(1-->3)-alpha-D-Glc pNAc-OMe.

作者信息

Pozsgay V, Coxon B

机构信息

Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, MD 20892, USA.

出版信息

Carbohydr Res. 1995 Nov 7;277(1):171-8. doi: 10.1016/0008-6215(95)00198-3.

DOI:10.1016/0008-6215(95)00198-3

PMID:8548787

Abstract

摘要

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Stereoselective preparation of alkyl glycosides of 2-acetamido-2-deoxy-alpha-D-glucopyranose by nonclassical halide-ion catalysis and synthesis and NMR spectroscopy of alpha-D-Gal p-(1-->3)-alpha-D-Glc pNAc-OMe.通过非经典卤离子催化立体选择性制备2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖的烷基糖苷以及α-D-半乳糖p-(1→3)-α-D-葡萄糖pNAc-OMe的合成与核磁共振光谱分析

Carbohydr Res. 1995 Nov 7;277(1):171-8. doi: 10.1016/0008-6215(95)00198-3.

Synthesis of Hex p-(1-->4)-beta-D-Glc pNAc-(1-->2)-alpha-D-Man p-(1-->O)(CH2)7CH3 probes for exploration of the substrate specificity of glycosyltransferases: Part I, Hex = beta-D-Gal, 4-deoxy-beta-D-Gal, 4-O-methyl-beta-D-Gal, 4-deoxy-4-fluoro-beta-D-Gal, or beta-D-Glc.用于探索糖基转移酶底物特异性的己糖对-(1→4)-β-D-葡糖胺-(1→2)-α-D-甘露糖-(1→O)(CH₂)₇CH₃探针的合成：第一部分，己糖 = β-D-半乳糖、4-脱氧-β-D-半乳糖、4-O-甲基-β-D-半乳糖、4-脱氧-4-氟-β-D-半乳糖或β-D-葡萄糖。

Carbohydr Res. 1996 Sep 23;291:63-83. doi: 10.1016/s0008-6215(96)00154-1.

Synthesis of cis-(1-->3)-glycosides of allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside.烯丙基 2-乙酰氨基-4,6-O-亚苄基-2-脱氧-α-D-吡喃葡萄糖苷的顺式-(1→3)-糖苷的合成

Carbohydr Res. 2004 May 17;339(7):1293-300. doi: 10.1016/j.carres.2004.01.014.

[Synthesis of terminal disaccharide of Forssman antigen and its analogs as spacer glycosides and free disaccharides].[福斯曼抗原末端二糖及其类似物作为间隔糖苷和游离二糖的合成]

Bioorg Khim. 1997 Jan;23(1):61-74.

All-aqueous, regiospecific transglycosylation synthesis of 3-O-alpha-L-fucopyranosyl-2-acetamido-2-deoxy-D-glucopyranose, a building block for the synthesis of branched oligosaccharides.3-O-α-L-呋喃岩藻糖基-2-乙酰氨基-2-脱氧-D-吡喃葡萄糖的全水相区域特异性转糖基化合成，一种用于合成支链寡糖的结构单元。

Biochem Biophys Res Commun. 1997 May 19;234(2):358-61. doi: 10.1006/bbrc.1997.6630.

Synthesis of disaccharide glycosyl donors suitable for introduction of the beta-D-Gal p-(1-->3)-alpha-and-beta-D-Gal pNAc groups.适用于引入β-D-半乳糖基-(1→3)-α-和β-D-半乳糖胺基的二糖糖基供体的合成。

Carbohydr Res. 1995 Jul 21;272(1):1-7. doi: 10.1016/0008-6215(95)00026-p.

The use of 2-deoxy-2-trichloroacetamido-D-glucopyranose derivatives in syntheses of oligosaccharides.2-脱氧-2-三氯乙酰氨基-D-吡喃葡萄糖衍生物在寡糖合成中的应用。

Carbohydr Res. 1994 Jul 16;260(2):189-202. doi: 10.1016/0008-6215(94)84038-5.

Syntheses of spacer-armed carbohydrate components of the Mycobacterium avium serocomplex serovar 8.

Carbohydr Res. 1997 Jan 2;297(2):153-61. doi: 10.1016/s0008-6215(96)00255-8.

Synthesis of allyl 3-deoxy- and 4-deoxy-beta-D-galactopyranoside and simultaneous preparations of Gal(1-->2)- and Gal(1-->3)-linked disaccharide glycosides.烯丙基 3-脱氧-β-D-吡喃半乳糖苷和 4-脱氧-β-D-吡喃半乳糖苷的合成以及 Gal(1→2)-和 Gal(1→3)-连接的二糖糖苷的同步制备。

Carbohydr Res. 1994 Jan 3;251:69-79. doi: 10.1016/0008-6215(94)84276-0.

Stereoselective synthesis of O-serinyl/threoninyl-2-acetamido-2-deoxy-alpha- or beta-glycosides.O-丝氨酰基/苏氨酰基-2-乙酰氨基-2-脱氧-α-或β-糖苷的立体选择性合成。

Carbohydr Res. 1995 Sep 8;274:11-28. doi: 10.1016/0008-6215(95)00016-m.

引用本文的文献

Protein conjugates of synthetic saccharides elicit higher levels of serum IgG lipopolysaccharide antibodies in mice than do those of the O-specific polysaccharide from Shigella dysenteriae type 1.与来自1型痢疾志贺氏菌的O特异性多糖的蛋白缀合物相比，合成糖类的蛋白缀合物在小鼠中引发更高水平的血清IgG脂多糖抗体。

Proc Natl Acad Sci U S A. 1999 Apr 27;96(9):5194-7. doi: 10.1073/pnas.96.9.5194.

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Stereoselective preparation of alkyl glycosides of 2-acetamido-2-deoxy-alpha-D-glucopyranose by nonclassical halide-ion catalysis and synthesis and NMR spectroscopy of alpha-D-Gal p-(1-->3)-alpha-D-Glc pNAc-OMe.

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