Chemoenzymatic syntheses of (-)-1-deoxymannojirimycin (DMJ) and its naturally occurring 6-O-alpha-L-rhamnopyranosyl glycoside.
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.
Banwell
Martin G
MG
Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia. mgb@rsc.anu.edu.au
Ma
Xinghua
X
Asano
Naoki
N
Ikeda
Kyoko
K
Lambert
John N
JN
D017485:1-Deoxynojirimycin / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002396:Catechols / Q000737:chemistry; D002417:Cattle; D002722:Chlorobenzenes / Q000737:chemistry / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D010084:Oxidation-Reduction; D051381:Rats; D012210:Rhamnose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D013237:Stereoisomerism
D002396:Catechols; D002722:Chlorobenzenes; D004791:Enzyme Inhibitors; D006027:Glycosides; D017485:1-Deoxynojirimycin; D006026:Glycoside Hydrolases; D012210:Rhamnose