参与胰岛素细胞内信号传导过程的糖基 - 肌醇合成的构建模块。

Building blocks for the synthesis of glycosyl-myo-inositols involved in the insulin intracellular signalling process.

作者信息

Zapata A, Martín-Lomas M

机构信息

Grupo de Carbohidratos, Instituto de Química Orgánica, C.S.I.C., Madrid, Spain.

出版信息

Carbohydr Res. 1992 Oct 9;234:93-106. doi: 10.1016/0008-6215(92)85041-w.

DOI:10.1016/0008-6215(92)85041-w

PMID:1468083

Abstract

Glycosylation of (+/- )-1-O-benzyl-2,3:5,6-di-O-isopropylidene-myo-inositol (4) with 6-O-acetyl-4-O-allyl-2-azido-3-O-benzyl-2-deoxy-beta-D-glucopyranosyl trichloroacetimidate (6) gave the 4-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)- myo-inositol derivative (9) as a mixture of diastereoisomers which could be resolved by chromatography. Likewise alpha-glycosylation of 4 with 6-O-acetyl-2-azido-3-O-benzoyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-beta- D- galactopyranosyl)-D-glucopyranosyl trichloroacetimidate (10) gave the corresponding pseudotrisaccharide derivative 16 as a mixture of diastereomers which could be resolved partially by chromatography. alpha-Glycosylation of enantiomerically pure 2,3:5,6- (18) and 2,3:4,5-di-O-isopropylidene-1-O-menthoxycarbonyl-myo-inositol (19) with 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate (20) gave the pseudodisaccharide derivatives 21 and 22, respectively. Likewise, alpha-glycosylation of 18 with 10 afforded a pseudotrisaccharide derivative (23).

摘要

将（±）-1-O-苄基-2,3:5,6-二-O-异亚丙基-myo-肌醇（4）与6-O-乙酰基-4-O-烯丙基-2-叠氮基-3-O-苄基-2-脱氧-β-D-吡喃葡萄糖基三氯乙酰亚胺酯（6）进行糖基化反应，得到4-O-（2-氨基-2-脱氧-α-D-吡喃葡萄糖基）-myo-肌醇衍生物（9），其为非对映异构体混合物，可通过色谱法分离。同样，4与6-O-乙酰基-2-叠氮基-3-O-苯甲酰基-2-脱氧-4-O-（2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基）-D-吡喃葡萄糖基三氯乙酰亚胺酯（10）进行α-糖基化反应，得到相应的假三糖衍生物16，其为非对映异构体混合物，可通过色谱法部分分离。对映体纯的2,3:5,6-（18）和2,3:4,5-二-O-异亚丙基-1-O-薄荷氧基羰基-myo-肌醇（19）与3,4,6-三-O-乙酰基-2-叠氮基-2-脱氧-D-吡喃葡萄糖基三氯乙酰亚胺酯（20）进行α-糖基化反应，分别得到假二糖衍生物21和22。同样，18与10进行α-糖基化反应得到假三糖衍生物（23）。