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1. (Article ID: 12189)
Ganci WM, Kuruüzüm A, Calis I, Rüedi P
Determination of the absolute configuration of (−)-(3R)-O-β-D-glucopyranosyloxy-5-phenylpentanoic acid from Polygonum salicifolium
Chirality 12(3) (2000)
139-142
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.
absolute configuration, methyl (+)-(R)- and (−)-(S)-3-hydroxy-5-phenylpentanoates, chiral HPLC, enantioselective hydrogenation, baker’s yeast reduction
NCBI PubMed ID: 10689292Publication DOI: 10.1002/(SICI)1520-636X(2000)12:3<139::AID-CHIR6>3.0.CO;2-3Journal NLM ID: 8914261Publisher: New York, NY: Wiley
Correspondence: Rüedi P
oci.unizh.ch>
Institutions: Hacettepe University, Faculty of Pharmacy, Department of Pharmacognosy, Ankara, Turkey, University of Zurich, Institute of Organic Chemistry, Zürich, Switzerland
Methods: 1H NMR, methylation, HPLC, enzymatic digestion, extraction, optical rotation measurement, reduction, CC, evaporation
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