Determination of the absolute configuration of (-)-(3R)-O-beta-D-glucopyranosyloxy-5-phenylpentanoic acid from Polygonum salicifolium
CHIRALITY, vol.12, no.3, pp.139-142, 2000 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 12 Issue: 3
- Publication Date: 2000
- Journal Name: CHIRALITY
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Page Numbers: pp.139-142
- Hacettepe University Affiliated: Yes
Abstract
The absolute configuration of the title compound has been determined after its enzymatic hydrolysis to 3-hydroxy-5-phenylpentanoic acid, esterification, and identification of the enantiomerically pure methyl (3R)-hydroxy-5-phenylpentanoate by HPLC on Chiralcel(R)OD-H. For reasons of inconsistent literature data, enantioselective reductions of methyl 3-oxo-5-phenylpentanoate have been reinspected and the stereochemical outcome unequivocally confirmed by both chiroptical and HPLC retention data. Chirality 12:139-142, 2000. (C) 2000 Wiley-Liss, Inc.