A convergent strategy for the critical .beta.-linked chitobiosyl-N-glycopeptide core
A convergent strategy for the critical .beta.-linked chitobiosyl-N-glycopeptide core
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关键β-连接的壳二糖基-N-糖肽核心的聚合策略
DOI：
10.1021/ja00062a064
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发表时间：
1993
影响因子：
15
通讯作者：
B. Fraser
中科院分区：
文献类型：
--
作者：
A. L. Handlon;B. Fraser
最近关于糖蛋白在细胞分裂和结合事件中的作用的研究2· 3促使人们对这些结构的化学合成产生了浓厚的兴趣。从细胞膜中分离出的糖蛋白具有多种结构，但大多数都有一个共同的核心，其中壳二糖残基通过N-3键连接到天冬酰胺l的甲酰胺上。[4]因此，这一关键连接最常见于Jeanloz的方法[5· 6]，其中糖基叠氮化物被还原为糖胺，并在碳二亚胺或另一种脱水剂的作用下与天冬氨酸和/或含天冬酰的肽缩合。7-9该方法通常由于产生葡糖胺的异构化而复杂化，即异构化混合物。从相应的糖基溴化物获得的8· 10糖基异硫氰酸酯也已经与天冬氨酸偶联以产生酰胺键。11· 12
Recent investigations concerning the role of glycoproteins in the mediation of cellular recognitionand binding events2· 3 have prompted intensified interest in the chemical syntheses of these structures. The glycoproteins that have been isolated from cell membranes display a diversity of structures, but most share a common core in which a chitobiose residue is attached through a/3-N linkage to the carboxamide of asparagine l. 4 Heretofore this key linkage has been made mostoften by Jeanloz’s methodology5· 6 inwhich a glycosyl azide is reduced to the glycosylamine and condensed with aspartic acid and/or aspartoylcontaining peptide under the agency of carbodiimide or another dehydrating agent. 7-9 This method is often complicated by the anomerization of the glycosylamine generating, ß mixtures. 8· 10 Glycosyl isothiocyanates, obtainable from the corresponding glycosyl bromides, have also been coupled with aspartic acid to yield amide linkages. 11· 12