Ovchinnikova T V, Ter-Grigorian A G, Pazynina G V, Bovin N V
Bioorg Khim. 1997 Jan;23(1):61-74.
Spacered terminal disaccharide of Forssman's antigen GalNAc alpha 1-3GalNAc beta 1-Osp, its analog GalNAc alpha 1-3GalNAc alpha 1-Osp, and disaccharides Gal beta 1-3GalNAc beta 1-Osp and Gal alpha 1-3GalNAc alpha 1-Osp [where sp denotes the (CH2)3NHCOCF3 spacer] were synthesized. Spacered disaccharides were obtained from the (3-trifluoroacetamidopropyl)-2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D- galactopyranoside and its alpha- and beta-analogs in which the 2-azido group was substituted for the 2-acetamido group. The azide glycosyl acceptors gave higher yields of the disaccharides. Azide glycosyl acceptors were prepared by the stereoselective glycosylation of 3-trifluoroacetamidopropanol with a mixture of 1-O-acetates of the 2-azido-3,4,6-tri-O-acetyl-2-deoxy-D-galactopyranose anomers in the presence of Lewis acids. Disaccharides Gal alpha 1-3GalNAc and GalNAc alpha 1-3GalNAc were obtained from the benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranoside.
合成了福斯曼抗原的间隔末端二糖GalNAcα1-3GalNAcβ1-Osp、其类似物GalNAcα1-3GalNAcα1-Osp以及二糖Galβ1-3GalNAcβ1-Osp和Galα1-3GalNAcα1-Osp[其中sp表示(CH2)3NHCOCF3间隔基]。间隔二糖由(3-三氟乙酰氨基丙基)-2-乙酰氨基-4,6-O-亚苄基-2-脱氧-β-D-吡喃半乳糖苷及其α-和β-类似物制得，其中2-叠氮基取代了2-乙酰氨基。叠氮糖基受体生成的二糖产率更高。叠氮糖基受体通过在路易斯酸存在下，3-三氟乙酰氨基丙醇与2-叠氮基-3,4,6-三-O-乙酰基-2-脱氧-D-吡喃半乳糖异头物的1-O-乙酸酯混合物进行立体选择性糖基化反应制备。二糖Galα1-3GalNAc和GalNAcα1-3GalNAc由苄基2-乙酰氨基-4,6-O-亚苄基-2-脱氧-α-D-吡喃半乳糖苷制得。
