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Mixed Aromatic Acyloin Condensations with Recombinant Benzaldehyde Lyase: Synthesis of α‐Hydroxydihydrochalcones and Related α‐Hydroxy Ketones
Author(s) -
SanchezGonzalez Monica,
Rosazza John P. N.
Publication year - 2003
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200303033
Subject(s) - chemistry , phenylacetaldehyde , benzaldehyde , synthon , organic chemistry , condensation reaction , stereochemistry , recombinant dna , catalysis , biochemistry , gene
Recombinant benzaldehyde lyase (BAL), expressed and purified from E. coli strain JM‐109, was used to catalyze the condensation of a series of methoxybenzaldehydes and phenylacetaldehyde in the synthesis of α‐( R )‐hydroxydihydrochalcones. Enantiomerically pure 1‐hydroxy‐1,3‐diphenylpropan‐2‐ones and o ‐anisoin were also obtained as products of the BAL reaction. The R absolute configurations of chiral centers were determined by CD spectroscopy. α‐( R )‐Hydroxydihydrochalcones and 1‐hydroxy‐1,3‐diphenylpropan‐2‐ones are valuable synthons for chemoenzymatic syntheses of flavonoids. This is the first synthesis of α‐( R )‐hydroxydihydrochalcones by a microbial enzyme.