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Titolo:
Switched enantiopreference of Humicola lipase for 2-phenoxyalkanoic acid ester homologs can be rationalized by different substrate binding modes
Autore:
Berglund, P; Vallikivi, I; Fransson, L; Dannacher, H; Holmquist, M; Martinelle, M; Bjorkling, F; Parve, O; Hult, K;
Indirizzi:
Royal Inst Technol, Dept Biotechnol, SE-10044 Stockholm, Sweden Royal InstTechnol Stockholm Sweden SE-10044 SE-10044 Stockholm, Sweden Tallinn Tech Univ, Inst Chem, Dept Bioorgan Chem, Tallinn 12618, Estonia Tallinn Tech Univ Tallinn Estonia 12618 gan Chem, Tallinn 12618, Estonia Leo Pharmaceut Prod, DK-2750 Ballerup, Denmark Leo Pharmaceut Prod Ballerup Denmark DK-2750 , DK-2750 Ballerup, Denmark
Titolo Testata:
TETRAHEDRON-ASYMMETRY
fascicolo: 21, volume: 10, anno: 1999,
pagine: 4191 - 4202
SICI:
0957-4166(19991029)10:21<4191:SEOHLF>2.0.ZU;2-Q
Fonte:
ISI
Lingua:
ENG
Soggetto:
CANDIDA-RUGOSA LIPASE; LANUGINOSA LIPASE; QUANTITATIVE-ANALYSES; SUBTILISIN CARLSBERG; NUCLEIC-ACIDS; FORCE-FIELD; ENANTIOMERS; BIOCATALYSIS; RESOLUTION; BIOTRANSFORMATIONS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
32
Recensione:
Indirizzi per estratti:
Indirizzo: Berglund, P Royal Inst Technol, Dept Biotechnol, SE-10044 Stockholm, Sweden Royal Inst Technol Stockholm Sweden SE-10044 ockholm, Sweden
Citazione:
P. Berglund et al., "Switched enantiopreference of Humicola lipase for 2-phenoxyalkanoic acid ester homologs can be rationalized by different substrate binding modes", TETRAHEDR-A, 10(21), 1999, pp. 4191-4202

Abstract

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)-enantiomerpreference 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 foundthat 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.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 03/12/20 alle ore 05:10:15