非对映异构烷基化假二糖作为海藻糖酶潜在亲和试剂的合成与评价

Synthesis and evaluation of diastereoisomeric alkylating pseudo-disaccharides as potential affinity reagents for trehalase.

作者信息

Bar-Guilloux E, Defaye J, Lehmann J, Nardin R, Robic D, Urbahns K

机构信息

Université de Caen, UFR des Sciences Pharmaceutiques, France.

出版信息

Carbohydr Res. 1993 Dec 16;250(1):1-8. doi: 10.1016/0008-6215(93)84149-z.

DOI:10.1016/0008-6215(93)84149-z

PMID:8143285

Abstract

Reaction of (+/-)-(3/4,5,6)-4-bromo-5,6-epoxy-3-hydroxycyclohexene with 2,3,4,6-tetra-O-acetyl-1-thio-alpha-D-glucopyranose, followed by treatment of the resulting isolated diastereoisomeric 4-bromo-3,5-dihydroxycyclohexene 1-thioglycoside derivatives with base under phase-transfer conditions, gave (R)- and (S)-(3,4,6/5)-3,4-epoxy-6-S-(1-thio-alpha-D-glucopyranosyl)-5- hydroxycyclohexene. None of them was substrate or inhibitor for cockchafer trehalase.

摘要

(±)-(3/4,5,6)-4-溴-5,6-环氧-3-羟基环己烯与2,3,4,6-四-O-乙酰基-1-硫代-α-D-吡喃葡萄糖反应，然后在相转移条件下用碱处理所得分离出的非对映异构的4-溴-3,5-二羟基环己烯1-硫代糖苷衍生物，得到(R)-和(S)-(3,4,6/5)-3,4-环氧-6-S-(1-硫代-α-D-吡喃葡萄糖基)-5-羟基环己烯。它们均不是金龟子海藻糖酶的底物或抑制剂。