Asymmetric synthesis of (S)-3-chloro-1-phenyl-1-propanol using Saccharomyces cerevisiae reductase with high enantioselectivity

Cited 26 time in scopus
Metadata Downloads

Full metadata record

DC FieldValueLanguage
dc.contributor.authorY H Choi-
dc.contributor.authorH J Choi-
dc.contributor.authorDoo Il Kim-
dc.contributor.authorK N Uhm-
dc.contributor.authorH K Kim-
dc.date.accessioned2017-04-19T09:18:51Z-
dc.date.available2017-04-19T09:18:51Z-
dc.date.issued2010-
dc.identifier.issn0175-7598-
dc.identifier.uri10.1007/s00253-010-2442-5ko
dc.identifier.urihttps://oak.kribb.re.kr/handle/201005/9571-
dc.description.abstract3-Chloro-1-phenyl-1-propanol is used as a chiral intermediate in the synthesis of antidepressant drugs. Various microbial reductases were expressed in Escherichia coli, and their activities toward 3-chloro-1-phenyl-1-propanone were evaluated. The yeast reductase YOL151W (GenBank locus tag) exhibited the highest level of activity and exclusively generated the (S)-alcohol. Recombinant YOL151W was purified by Ni-nitrilotriacetic acid (Ni-NTA) and desalting column chromatography. It displayed an optimal temperature and pH of 40°C and 7.5-8.0, respectively. The glucose dehydrogenase coupling reaction was introduced as an NADPH regeneration system. NaOH solution was occasionally added to maintain the reaction solution pH within the range of 7.0-7.5. By using this reaction system, the substrate (30 mM) could be completely converted to the (S)-alcohol product with an enantiomeric excess value of 100%. A homology model of YOL151W was constructed based on the structure of Sporobolomyces salmonicolor carbonyl reductase (Protein Data Bank ID: 1Y1P). A docking model of YOL151W with NADPH and 3-chloro-1-phenyl-1-propanone was then constructed, which showed that the cofactor and substrate bound tightly to the active site of the enzyme in the lowest free energy state and explained how the (S)-alcohol was produced exclusively in the reduction process.-
dc.publisherSpringer-
dc.titleAsymmetric synthesis of (S)-3-chloro-1-phenyl-1-propanol using Saccharomyces cerevisiae reductase with high enantioselectivity-
dc.title.alternativeAsymmetric synthesis of (S)-3-chloro-1-phenyl-1-propanol using Saccharomyces cerevisiae reductase with high enantioselectivity-
dc.typeArticle-
dc.citation.titleApplied Microbiology and Biotechnology-
dc.citation.number1-
dc.citation.endPage193-
dc.citation.startPage185-
dc.citation.volume87-
dc.contributor.affiliatedAuthorDoo Il Kim-
dc.contributor.alternativeName최윤희-
dc.contributor.alternativeName최혜정-
dc.contributor.alternativeName김두일-
dc.contributor.alternativeName엄기남-
dc.contributor.alternativeName김형권-
dc.identifier.bibliographicCitationApplied Microbiology and Biotechnology, vol. 87, no. 1, pp. 185-193-
dc.identifier.doi10.1007/s00253-010-2442-5-
dc.subject.keywordAntidepressant drugs-
dc.subject.keywordChiral intermediate-
dc.subject.keywordDocking model-
dc.subject.keywordEnantioselectivity-
dc.subject.keywordReductase-
dc.subject.localAntidepressant drugs-
dc.subject.localChiral intermediate-
dc.subject.localDocking model-
dc.subject.localEnantioselectivity-
dc.subject.localReductase-
dc.description.journalClassY-
Appears in Collections:
1. Journal Articles > Journal Articles
Files in This Item:
  • There are no files associated with this item.


Items in OpenAccess@KRIBB are protected by copyright, with all rights reserved, unless otherwise indicated.