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[合成作为N-乙酰葡糖胺基转移酶I底物的N-糖蛋白修饰寡糖]

[Synthesis of modified oligosaccharides of the N-glycoprotein as substrate for N-acetylglucosaminyltransferase I].

作者信息

Paulsen H, Reck F, Brockhausen I

机构信息

Institut für Organische Chemie, Universität Hamburg, Deutschland.

出版信息

Carbohydr Res. 1992 Dec 15;236:39-71. doi: 10.1016/0008-6215(92)85006-l.

DOI:10.1016/0008-6215(92)85006-l
PMID:1291062
Abstract

In the synthesis of modified derivatives of octyl O-(alpha-D-mannopyranosyl)-(1-->3)-O-[(alpha-D-mannopyranosyl)-(1-->6)]- beta-D-mannopyranoside, 4.,5-epoxypentyl, a 4-diazirinopentyl, and a 5-(iodoacetamido)pentyl group were attached to the 3''-OH of the trisaccharide. The diazirino derivative may be especially suitable for photolabeling of the active site of N-acetylglucosaminyltransferase I (GlcNAcT-I). In addition, the 2'-OH group of the above-mentioned trisaccharide was reduced to a 2'-deoxy group and substituted 2'-O-methyl group.

摘要

在辛基O-(α-D-吡喃甘露糖基)-(1→3)-O-[(α-D-吡喃甘露糖基)-(1→6)]-β-D-吡喃甘露糖苷的修饰衍生物合成中，4,5-环氧戊基、4-重氮环戊基和5-(碘乙酰胺基)戊基连接到三糖的3''-OH上。重氮环戊基衍生物可能特别适用于N-乙酰葡糖胺基转移酶I（GlcNAcT-I）活性位点的光标记。此外，上述三糖的2'-OH基团被还原为2'-脱氧基团并被2'-O-甲基取代。

相似文献

1
[Synthesis of modified oligosaccharides of the N-glycoprotein as substrate for N-acetylglucosaminyltransferase I].[合成作为N-乙酰葡糖胺基转移酶I底物的N-糖蛋白修饰寡糖]
Carbohydr Res. 1992 Dec 15;236:39-71. doi: 10.1016/0008-6215(92)85006-l.
2
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引用本文的文献

1
Hans Paulsen: Contributions to the Investigations of Glycoprotein Biosynthesis.汉斯·保尔森：对糖蛋白生物合成研究的贡献。
Molecules. 2025 Sep 14;30(18):3735. doi: 10.3390/molecules30183735.
2
Synthetic substrate analogues for UDP-GlcNAc: Man alpha 1-3R beta 1-2-N-acetylglucosaminyltransferase I. Substrate specificity and inhibitors for the enzyme.UDP-N-乙酰葡糖胺的合成底物类似物：甘露糖α1-3受体β1-2-N-乙酰葡糖胺基转移酶I。该酶的底物特异性和抑制剂。
Glycoconj J. 1995 Dec;12(6):747-54. doi: 10.1007/BF00731234.
3
Synthetic substrate analogues for UDP-GlcNAc: Man alpha 1-6R beta(1-2)-N-acetylglucosaminyltransferase II. Substrate specificity and inhibitors for the enzyme.
Glycoconj J. 1994 Jun;11(3):210-6. doi: 10.1007/BF00731220.
4
Insertion into Aspergillus nidulans of functional UDP-GlcNAc: alpha 3-D- mannoside beta-1,2-N-acetylglucosaminyl-transferase I, the enzyme catalysing the first committed step from oligomannose to hybrid and complex N-glycans.将功能性UDP-GlcNAc：α3-D-甘露糖苷β-1,2-N-乙酰葡糖胺基转移酶I导入构巢曲霉，该酶催化从寡甘露糖到杂合型和复合型N-聚糖的首个关键步骤。
Glycoconj J. 1995 Jun;12(3):360-70. doi: 10.1007/BF00731339.