Synthesis of optically pure 2-azido-1-arylethanols with isolated enzymes and conversion to triazole-containing beta-blocker analogues employing click chemistry.
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.
Ankati
Haribabu
H
Department of Chemistry, Southern Methodist University, Dallas, Texas 75275, USA.
Yang
Yan
Y
Zhu
Dunming
D
Biehl
Edward R
ER
Hua
Ling
L
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*
D000098:Acetophenones; D000319:Adrenergic beta-Antagonists; D000480:Alkynes; D001386:Azides; D014230:Triazoles; D000431:Ethanol; D000429:Alcohol Oxidoreductases; D000426:Alcohol Dehydrogenase