title: Synthesis of optically pure 2-azido-1-arylethanols with isolated enzymes and conversion to triazole-containing beta-blocker analogues employing click chemistry.
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.
authors.affiliation: Department of Chemistry, Southern Methodist University, Dallas, Texas 75275, USA.
authors.forename: Haribabu
authors.initials: H
authors.lastname: Ankati
authors.forename: Yan
authors.initials: Y
authors.lastname: Yang
authors.forename: Dunming
authors.initials: D
authors.lastname: Zhu
authors.forename: Edward R
authors.initials: ER
authors.lastname: Biehl
authors.forename: Ling
authors.initials: L
authors.lastname: Hua
mesh_terms: D000098:Acetophenones / Q000737:chemistry; D000319:Adrenergic beta-Antagonists / Q000138:chemical synthesis*; D000426:Alcohol Dehydrogenase / Q000737:chemistry / Q000378:metabolism; D000429:Alcohol Oxidoreductases / Q000737:chemistry / Q000378:metabolism; D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000138:chemical synthesis; D002175:Candida / Q000201:enzymology; D000431:Ethanol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D012441:Saccharomyces cerevisiae / Q000201:enzymology; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis*
chemical_list: D000098:Acetophenones; D000319:Adrenergic beta-Antagonists; D000480:Alkynes; D001386:Azides; D014230:Triazoles; D000431:Ethanol; D000429:Alcohol Oxidoreductases; D000426:Alcohol Dehydrogenase