A novel approach to the 1-deoxynojirimycin system: Synthesis from sucrose of 2-acetamido-1,2-dideoxynojirimycin, as well as some 2-N-modified derivatives

被引：27

作者：

Gradnig, G

Legler, G

Stutz, AE

机构：

[1] GRAZ TECH UNIV,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA

[2] UNIV COLOGNE,INST BIOCHEM,D-50674 COLOGNE,GERMANY

来源：

CARBOHYDRATE RESEARCH | 1996年 / 287卷

关键词：

1-deoxynojirimycin; 2-acetamido-1,2-dideoxynojirimycin; glycosidase inhibitors; sucrose;

D O I：

10.1016/0008-6215(96)00065-1

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：

6-Azido-1,3,4-tri-O-benzyl-6-deoxy-D-fructofuranose can be easily obtained in two steps from the known 6,6'-diazido-6,6'-dideoxysucrose (available in two steps from sucrose) and cyclized by controlled hydrogenation and concomitant intramolecular reductive amination to give 3,4,6-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol, a partially protected derivative of 1-deoxymannojirimycin. After N-protection, position 2 is regio-specifically available to modification. This novel approach was taken advantage of in a synthesis of 2-acetamido-1,2-dideoxynojirimycin and new analogues thereof. Results of inhibition studies conducted with these new compounds employing N-acetylhexosaminidases of various sources are discussed. (C) 1996 Elsevier Science Ltd.

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页码：49 / 57

页数：9

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