Structural and Experimental Evidence for the Enantiomeric Recognition toward a Bulky sec-Alcohol by Candida antarctica Lipase B
DC Field | Value | Language |
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dc.contributor.author | Park, Areum | - |
dc.contributor.author | Kim, Sunmin | - |
dc.contributor.author | Park, Jeemin | - |
dc.contributor.author | Joe, Saerom | - |
dc.contributor.author | Min, Bora | - |
dc.contributor.author | Oh, Joonyoung | - |
dc.contributor.author | Song, Jaekwang | - |
dc.contributor.author | Park, SangYoun | - |
dc.contributor.author | Park, Seongsoon | - |
dc.contributor.author | Lee, Hyuk | - |
dc.date.available | 2018-05-09T02:11:47Z | - |
dc.date.created | 2018-04-17 | - |
dc.date.issued | 2016-11 | - |
dc.identifier.issn | 2155-5435 | - |
dc.identifier.uri | http://scholarworks.bwise.kr/ssu/handle/2018.sw.ssu/7468 | - |
dc.description.abstract | Candida antarctica lipase B (CAL-B) exhibits remarkable enantioselectivity for various chiral sec-alcohols, and the enantioselectivity is structurally well-understood. Two substituents at the chiral center of a sec-alcohol separately bind two pockets, namely, large and medium binding pockets. It has been believed that the medium pocket is too small to accommodate a large substituent (larger than an ethyl group), and thus, bulky sec alcohols bearing two large substituents have been regarded as a poor substrate for CAL-B. However, we found that CAL-B can catalyze the transesterification of N-Boc-protected rac-2-amino-1-phenylethanol (1a) enantioselectively with a moderate reaction rate. X-ray crystallography and computer modeling revealed that the rotation of the Leu278 side chain creates a space to accept the N-Boc-aminomethylene group of la. Moreover, a sec-alcohol substrate with less than one hydrogen atom at the gamma-position from the hydroxyl group is required to achieve a moderate reaction rate. On the basis of this observation, we diversified bulky N-Boc-protected rac-2-amino-1-arylethanols for the transesterifications with high enantioselectivities (E > 200). | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.relation.isPartOf | ACS CATALYSIS | - |
dc.subject | INDUSTRIAL APPLICATIONS | - |
dc.subject | KINETIC RESOLUTIONS | - |
dc.subject | SECONDARY ALCOHOLS | - |
dc.subject | RATIONAL REDESIGN | - |
dc.subject | ESCHERICHIA-COLI | - |
dc.subject | PICHIA-PASTORIS | - |
dc.subject | ACTIVE-SITE | - |
dc.subject | ENANTIOSELECTIVITY | - |
dc.subject | TEMPERATURE | - |
dc.subject | BIOCATALYSTS | - |
dc.title | Structural and Experimental Evidence for the Enantiomeric Recognition toward a Bulky sec-Alcohol by Candida antarctica Lipase B | - |
dc.type | Article | - |
dc.identifier.doi | 10.1021/acscatal.6b02192 | - |
dc.type.rims | ART | - |
dc.identifier.bibliographicCitation | ACS CATALYSIS, v.6, no.11, pp.7458 - 7465 | - |
dc.description.journalClass | 1 | - |
dc.identifier.wosid | 000387306100023 | - |
dc.identifier.scopusid | 2-s2.0-85033212734 | - |
dc.citation.endPage | 7465 | - |
dc.citation.number | 11 | - |
dc.citation.startPage | 7458 | - |
dc.citation.title | ACS CATALYSIS | - |
dc.citation.volume | 6 | - |
dc.contributor.affiliatedAuthor | Park, SangYoun | - |
dc.type.docType | Article | - |
dc.subject.keywordAuthor | 2-amino-1-phenylethanol | - |
dc.subject.keywordAuthor | bulky sec-alcohol | - |
dc.subject.keywordAuthor | lipase | - |
dc.subject.keywordAuthor | molecular modeling | - |
dc.subject.keywordAuthor | X-ray crystallography | - |
dc.subject.keywordPlus | INDUSTRIAL APPLICATIONS | - |
dc.subject.keywordPlus | KINETIC RESOLUTIONS | - |
dc.subject.keywordPlus | SECONDARY ALCOHOLS | - |
dc.subject.keywordPlus | RATIONAL REDESIGN | - |
dc.subject.keywordPlus | ESCHERICHIA-COLI | - |
dc.subject.keywordPlus | PICHIA-PASTORIS | - |
dc.subject.keywordPlus | ACTIVE-SITE | - |
dc.subject.keywordPlus | ENANTIOSELECTIVITY | - |
dc.subject.keywordPlus | TEMPERATURE | - |
dc.subject.keywordPlus | BIOCATALYSTS | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
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