Mixed Aromatic Acyloin Condensations with Recombinant Benzaldehyde Lyase: Synthesis of α-Hydroxydihydrochalcones and Related α-Hydroxy Ketones
✍ Scribed by Monica Sanchez-Gonzalez; John P. N. Rosazza
- Publisher
- John Wiley and Sons
- Year
- 2003
- Tongue
- English
- Weight
- 101 KB
- Volume
- 345
- Category
- Article
- ISSN
- 1615-4150
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✦ Synopsis
Abstract
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.