Mixed Aromatic Acyloin Condensations with Recombinant Benzaldehyde Lyase: Synthesis of α-Hydroxydihydrochalcones and Related α-Hydroxy Ketones

Autor:	John P. N. Rosazza, Monica Sanchez-Gonzalez
Rok vydání:	2003
Předmět:	chemistry.chemical_classification Phenylacetaldehyde Circular dichroism Benzaldehyde lyase Stereochemistry Acyloin condensation Flavonoid Synthon General Chemistry law.invention chemistry.chemical_compound chemistry law Microbial enzymes Recombinant DNA Organic chemistry
Zdroj:	Advanced Synthesis & Catalysis. 345:819-824
ISSN:	1615-4169 1615-4150
DOI:	10.1002/adsc.200303033
Popis:	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.
Databáze:	OpenAIRE
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