Chemoenzymatic syntheses of (-)-1-deoxymannojirimycin (DMJ) and its naturally occurring 6-O-alpha-L-rhamnopyranosyl glycoside | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

659778

Reference Type

Journal Article

Title

Chemoenzymatic syntheses of (-)-1-deoxymannojirimycin (DMJ) and its naturally occurring 6-O-alpha-L-rhamnopyranosyl glycoside

Author(s)

Banwell, MG; Ma, X; Asano, N; Ikeda, K; Lambert, JN

Year

2003

Is Peer Reviewed?

Journal

Organic and Biomolecular Chemistry
ISSN: 1477-0520
EISSN: 1477-0539

Volume

Issue

Page Numbers

2035-2037

Language

English

PMID

12945891

Abstract

The naturally occurring sugar mimetic alkaloids 1-deoxymannojirimycin (DMJ, 1) and 6-O-alpha-L-rhamnopyranosyl-DMJ (2) have each been prepared in a completely stereoselective manner from the cis-1,2-dihydrocatechol 3, itself obtained in enantiomerically pure form by microbial oxidation of chlorobenzene

Keywords

1-Deoxynojirimycin; analogs & derivatives; Animals; antagonists & inhibitors; Catechols; Cattle; chemical synthesis; chemistry; Chlorobenzenes; Enzyme Inhibitors; Glycoside Hydrolases; Glycosides; Humans; metabolism; Oxidation-Reduction; Pharmacology; Research; Rhamnose; Stereoisomerism