Determination of the absolute configuration of (-)-(3R)-O-beta-D-glucopyranosyloxy-5-phenylpentanoic acid from Polygonum salicifolium

Ganci W., Kuruuzum A. , Calis I., Ruedi P.

CHIRALITY, cilt.12, sa.3, ss.139-142, 2000 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 12 Konu: 3
  • Basım Tarihi: 2000
  • Dergi Adı: CHIRALITY
  • Sayfa Sayıları: ss.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. Chirality 12:139-142, 2000. (C) 2000 Wiley-Liss, Inc.