title: Determination of the absolute configuration of (-)-(3R)-O-beta-D-glucopyranosyloxy-5-phenylpentanoic acid from Polygonum salicifolium.
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.
authors.affiliation: University of Zurich, Institute of Organic Chemistry, Zürich, Switzerland.
authors.forename: W M
authors.initials: WM
authors.lastname: Ganci
authors.forename: A
authors.initials: A
authors.lastname: Kuruüzüm
authors.forename: I
authors.initials: I
authors.lastname: Caliş
authors.forename: P
authors.initials: P
authors.lastname: Rüedi
mesh_terms: D002851:Chromatography, High Pressure Liquid; D005960:Glucosides / Q000737:chemistry*; D019664:Polygonaceae / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005960:Glucosides; C406347:glucopyranosyloxy-5-phenylpentanoic acid