PERACETYLATED LAMINARIBIOSE - PREPARATION BY SPECIFIC DEGRADATION OF CURDLAN AND ITS CHEMICAL CONVERSION INTO N-ACETYLHYALOBIURONIC ACID

被引：34

作者：

WANG, LX ^{[1
]}

SAKAIRI, N ^{[1
]}

KUZUHARA, H ^{[1
]}

机构：

[1] INST PHYS & CHEM RES,WAKO,SAITAMA 35101,JAPAN

来源：

CARBOHYDRATE RESEARCH | 1991年 / 219卷

关键词：

D O I：

10.1016/0008-6215(91)89048-K

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

beta-Laminaribiose octaacetate (2b) was prepared in greater than 50% yield from the microbial polysaccharide curdlan by specific degradation with a yeast cell-wall lytic enzyme preparation, Kitalase, and subsequent acetylation. Acetolysis of curdlan also gave alpha-laminaribiose octaacetate (2a) in 27% yield. The usefulness of these peracetates 2a and 2b as starting materials for organic synthesis was shown by converting 2b into N-acetylhyalobiuronic acid (23), the disaccharide repeating unit of hyaluronic acid. The conversion was carried out via a series of reactions, which included azidonitration of the glucal derivative and selective alkylidenation or direct tritylation to discriminate two primary hydroxyl groups existing in the disaccharide intermediates.

引用

页码：133 / 148

页数：16

共 30 条

[1] THE SYNTHESIS OF LAMINARIBIOSE (3-BETA-D-GLUCOSYL D-GLUCOSE) AND PROOF OF ITS IDENTITY WITH LAMINARIBIOSE ISOLATED FROM LAMINARIN [J].