Simultaneous synthesis of enantiomerically pure (S)-amino acids and (R)-amines using alpha/omega-aminotransferase coupling reactions with two-liquid phase reaction system

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dc.contributor.authorCho, Byung-Kwanko
dc.contributor.authorCho, Ho Jungko
dc.contributor.authorPark, Sung-Heeko
dc.contributor.authorYun, Hyungdonko
dc.contributor.authorKim, Byung-Geeko
dc.date.accessioned2013-03-04T02:17:52Z-
dc.date.available2013-03-04T02:17:52Z-
dc.date.created2012-02-06-
dc.date.created2012-02-06-
dc.date.issued2003-12-
dc.identifier.citationJOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, v.26, pp.273 - 285-
dc.identifier.issn1381-1177-
dc.identifier.urihttp://hdl.handle.net/10203/81467-
dc.description.abstractAn efficient simultaneous synthesis of enantiopure (S)-amino acids and chiral (R)-amines was achieved using alpha/omega-aminotransferase (alpha/omega-AT) coupling reaction with two-liquid phase system. As, among the enzyme components in the alpha/omega-AT coupling reaction systems, only omega-AT is severely hampered by product inhibition by ketone product, the coupled reaction cannot be carried out above 60 mM substrates. To overcome this problem, a two-liquid phase reaction was chosen, where dioctylphthalate was selected as the solvent based upon biocompatibility, partition coefficient and effect on enzyme activity. Using 100 mM of substrates, the AroAT/omega-AT and the AlaAT/omega-AT coupling reactions asymmetrically synthesized (S)-phenylaianine and (S)-2-aminobutyrate with 93% (>99% ee(S)) and 95% (>99% ee(S)) of conversion yield, and resolved the racemic alpha-methylbenzylamine with 56% (95% ee(R)) and 54% (96% ee(R)) of conversion yield, respectively. Moreover, using 300 mM of 2-oxobutyrate and 300 mM of racemic alpha-methylbenzylamine as substrates, the coupling reactions yielded 276 mM of (S)-2-aminobutyrate (>99% ee) and 144 mM of (R)-alpha-methylbenzylamine (>96% ee) in 9 h. Here, most of the reactions take place in the aqueous phase, and acetophenone mainly moved to the organic phase according to its partition coefficient. (C) 2003 Published by Elsevier B.V.-
dc.languageEnglish-
dc.publisherELSEVIER SCIENCE BV-
dc.subjectUNNATURAL AMINO-ACIDS-
dc.subjectESCHERICHIA-COLI K-12-
dc.subjectASYMMETRIC-SYNTHESIS-
dc.subjectL-PHENYLALANINE-
dc.subjectKINETIC RESOLUTION-
dc.subjectOMEGA-TRANSAMINASE-
dc.subjectBIPHASIC SYSTEM-
dc.subjectCHIRAL AMINES-
dc.subjectBIOCATALYSIS-
dc.subjectBIOSYNTHESIS-
dc.titleSimultaneous synthesis of enantiomerically pure (S)-amino acids and (R)-amines using alpha/omega-aminotransferase coupling reactions with two-liquid phase reaction system-
dc.typeArticle-
dc.identifier.wosid000187060500021-
dc.identifier.scopusid2-s2.0-0242407524-
dc.type.rimsART-
dc.citation.volume26-
dc.citation.beginningpage273-
dc.citation.endingpage285-
dc.citation.publicationnameJOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC-
dc.identifier.doi10.1016/j.molcatb.2003.07.006-
dc.contributor.localauthorCho, Byung-Kwan-
dc.contributor.nonIdAuthorCho, Ho Jung-
dc.contributor.nonIdAuthorPark, Sung-Hee-
dc.contributor.nonIdAuthorYun, Hyungdon-
dc.contributor.nonIdAuthorKim, Byung-Gee-
dc.type.journalArticleArticle-
dc.subject.keywordAuthoraminotransferase-
dc.subject.keywordAuthorcoupling reaction-
dc.subject.keywordAuthorchiral amino acids-
dc.subject.keywordAuthoramines-
dc.subject.keywordAuthortwo-liquid phase reaction-
dc.subject.keywordPlusUNNATURAL AMINO-ACIDS-
dc.subject.keywordPlusESCHERICHIA-COLI K-12-
dc.subject.keywordPlusASYMMETRIC-SYNTHESIS-
dc.subject.keywordPlusL-PHENYLALANINE-
dc.subject.keywordPlusKINETIC RESOLUTION-
dc.subject.keywordPlusOMEGA-TRANSAMINASE-
dc.subject.keywordPlusBIPHASIC SYSTEM-
dc.subject.keywordPlusCHIRAL AMINES-
dc.subject.keywordPlusBIOCATALYSIS-
dc.subject.keywordPlusBIOSYNTHESIS-
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