Synthesis of optically pure 2-azido-1-arylethanols with isolated enzymes and conversion to triazole-containing beta-blocker analogues employing click chemistry

Haribabu Ankati; Yan Yang; Dunming Zhu; Edward R Biehl; Ling Hua

doi:10.1021/jo8009616

Synthesis of optically pure 2-azido-1-arylethanols with isolated enzymes and conversion to triazole-containing beta-blocker analogues employing click chemistry

J Org Chem. 2008 Aug 15;73(16):6433-6. doi: 10.1021/jo8009616. Epub 2008 Jul 16.

Authors

Haribabu Ankati¹, Yan Yang, Dunming Zhu, Edward R Biehl, Ling Hua

Affiliation

¹ Department of Chemistry, Southern Methodist University, Dallas, Texas 75275, USA.

PMID: 18630881
DOI: 10.1021/jo8009616

Abstract

Both antipodes of 2-azido-1-arylethanols were synthesized with excellent optical purity via enzymatic reduction of the corresponding alpha-azidoacetophenone derivatives catalyzed by a recombinant carbonyl reductase from Candida magnoliae ( CMCR) or an alcohol dehydrogenase from Saccharomyces cerevisiae ( Ymr226c). This provides an effective route to this class of important compounds in optically pure form. ( S)-2-Azido-1-( p-chlorophenyl)ethanols reacted with alkynes employing click chemistry to afford high yields of optically pure triazole-containing beta-adrenergic receptor blocker analogues with potential biological activity.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Acetophenones / chemistry
Adrenergic beta-Antagonists / chemical synthesis*
Alcohol Dehydrogenase / chemistry
Alcohol Dehydrogenase / metabolism
Alcohol Oxidoreductases / chemistry
Alcohol Oxidoreductases / metabolism
Alkynes / chemistry
Azides / chemical synthesis
Candida / enzymology
Ethanol / analogs & derivatives*
Ethanol / chemical synthesis
Saccharomyces cerevisiae / enzymology
Stereoisomerism
Triazoles / chemical synthesis*

Substances

Acetophenones
Adrenergic beta-Antagonists
Alkynes
Azides
Triazoles
Ethanol
Alcohol Oxidoreductases
Alcohol Dehydrogenase