Szabó L, Ramza J, Langdon C, Polt R
Department of Chemistry, University of Arizona, Tucson 85721, USA.
Carbohydr Res. 1995 Sep 8;274:11-28. doi: 10.1016/0008-6215(95)00016-m.
General glycosidation methodology has been developed which can selectively provide 2-acetamido-2-deoxy-alpha- or beta-glycosides of beta-hydroxy-alpha-amino acid derivatives [glucopyranoside-(8, 43), galactopyranoside- (9, 13), mannopyranoside- (10), lactoside analogs (11, 38) and 3-O-beta-galactopyranosyl-mannopyranoside (12)] stereoselectively in excellent yield from the highly nucleophilic alpha-imino esters (Schiff bases) of L-serine and L-threonine. Various glycosides were converted via their amino and acetamido derivatives to Fmoc-protected serinyl- or threoninyl-glycosides (24-28, 37, 41, 46) which are all suitable building blocks for the solid-phase synthesis of O-glycopeptides. Complete 1H- and 13C-NMR data are provided for all compounds.
已经开发出通用的糖基化方法，该方法可以从L-丝氨酸和L-苏氨酸的高亲核性α-亚氨基酯（席夫碱）中以优异的产率立体选择性地提供β-羟基-α-氨基酸衍生物的2-乙酰氨基-2-脱氧-α-或β-糖苷[吡喃葡萄糖苷-(8, 43)、吡喃半乳糖苷-(9, 13)、吡喃甘露糖苷-(10)、乳糖苷类似物(11, 38)和3-O-β-吡喃半乳糖基-吡喃甘露糖苷(12)]。各种糖苷通过其氨基和乙酰氨基衍生物转化为Fmoc保护的丝氨酰基或苏氨酰基糖苷(24 - 28, 37, 41, 46)，这些都是用于O-糖肽固相合成的合适构件。提供了所有化合物完整的1H和13C-NMR数据。
