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Switched enantiopreference of Humicola lipase for 2-phenoxyalkanoic acid ester homologs can be rationalized by different substrate binding modes
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- Berglund, Per (author)
- KTH,Bioteknologi
- Vallikivi, I. (author)
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- Fransson, Linda (author)
- KTH,Bioteknologi
- show more...
- Dannacher, H. (author)
- Björkling, F. (author)
- Parve, O. (author)
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- (creator_code:org_t)
- 1999
- 1999
- English.
- In: Tetrahedron. - 0957-4166 .- 1362-511X. ; 10:21, s. 4191-4202
- Journal article (peer-reviewed)
Abstract
Subject headings
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- Humicola lanuginosa lipase was used for enantioselective hydrolyses of a series of homologous 2-phenoxyalkanoic acid ethyl esters. The enantioselectivity (E-value) of the enzyme changed from an (R)-enantiomer preference for the smallest substrate, 2-phenoxypropanoic acid ester, to an (S)-enantiomer preference for the homologous esters with longer acyl moieties. The E-values span the range from E=13 (R) to E=56 (S). A molecular modeling study identified two different substrate-binding modes for each enantiomer. We found that the enantiomers favored different modes. This discovery provided a model that offered a rational explanation for the observed switch in enantioselectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.
Subject headings
- NATURVETENSKAP -- Biologi -- Biokemi och molekylärbiologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences -- Biochemistry and Molecular Biology (hsv//eng)
Keyword
- CANDIDA-RUGOSA LIPASE
- LANUGINOSA LIPASE
- QUANTITATIVE-ANALYSES
- SUBTILISIN CARLSBERG
- NUCLEIC-ACIDS
- FORCE-FIELD
- ENANTIOMERS
- BIOCATALYSIS
- RESOLUTION
- BIOTRANSFORMATIONS
- Biochemistry
- Biokemi
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- ref (subject category)
- art (subject category)
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- Berglund, Per
- Vallikivi, I.
- Fransson, Linda
- Dannacher, H.
- Holmquist, Mats
- Martinelle, Mats
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- Björkling, F.
- Parve, O.
- Hult, Karl
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- About the subject
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- NATURAL SCIENCES
- NATURAL SCIENCES
- and Biological Scien ...
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- Articles in the publication
- Tetrahedron
- By the university
- Royal Institute of Technology
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