Whole-cell mediated 11 beta-hydroxylation on the basic limonoid skeleton by cunninghamella echinulata

TitleWhole-cell mediated 11 beta-hydroxylation on the basic limonoid skeleton by cunninghamella echinulata
Publication TypeJournal Article
Year of Publication2015
AuthorsHaldar, S, Mulani, FA, Aarthy, T, Thulasiram, HV
JournalJournal of Organic Chemistry
Volume80
Issue12
Pagination6490-6495
Date PublishedJUN
ISSN0022-3263
Abstract

Regio- and stereoselective 11 beta-hydroxylation was achieved on the basic limonoid skeleton through microbial transformation. Whole cells of Cunninghamella echinulata efficiently converted basic limonoids such as epoxyazadiradione, azadiradione, and gedunin to their 11 beta-hydroxy analogues as the sole metabolite. Fermentation conditions affecting the efficiency (96%) of biotransformation including substrate concentration, incubation period, pH, and temperature were optimized. The position and stereochemistry of hydroxyl functionality on the isolated metabolites were established through extensive spectroscopic and spectrometric studies (1D, 2D NMR, ESI-MS, and MS/MS).

DOI10.1021/acs.joc.5b00417
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.785

Divison category: 
Organic Chemistry