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Titolo:
Molecular basis for the stereospecificity of Candida rugosa lipase (CRL) towards ibuprofen
Autore:
Lakshmi, BS; Kangueane, P; Guo, Y; Chen, YZ; Gautam, P;
Indirizzi:
Anna Univ, Ctr Biotechnol, Chennai 600025, India Anna Univ Chennai India600025 iv, Ctr Biotechnol, Chennai 600025, India Natl Univ Singapore, Dept Computat Sci, Singapore, Singapore Natl Univ Singapore Singapore Singapore putat Sci, Singapore, Singapore
Titolo Testata:
BIOCATALYSIS AND BIOTRANSFORMATION
fascicolo: 6, volume: 17, anno: 2000,
pagine: 475 - 486
SICI:
1024-2422(2000)17:6<475:MBFTSO>2.0.ZU;2-N
Fonte:
ISI
Lingua:
ENG
Soggetto:
ORGANIC-SOLVENTS; CATALYZED ESTERIFICATION; INTERFACIAL ACTIVATION; ENZYMATIC CATALYSIS; SYNTHASE ISOZYME-1; RACEMIC IBUPROFEN; BINDING; ESTER; MEDIA; PHARMACOKINETICS;
Keywords:
ibuprofen; P2O5; Candida rugosa lipase; stereospecificity; molecular modelling;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
38
Recensione:
Indirizzi per estratti:
Indirizzo: Gautam, P Anna Univ, Ctr Biotechnol, Chennai 600025, India Anna Univ Chennai India 600025 otechnol, Chennai 600025, India
Citazione:
B.S. Lakshmi et al., "Molecular basis for the stereospecificity of Candida rugosa lipase (CRL) towards ibuprofen", BIOCATAL B, 17(6), 2000, pp. 475-486

Abstract

The stereospecific esterification of ibuprofen by Candida rugosa lipase (CRL) with 1-butanol was optimised. The yield of the butyl ester was nearly quantitative with an enantiomeric excess of 95% and E > 100. Enzyme desiccation over P2O5 had a pronounced effect on the esterification yield and its role in stereospecificity is discussed. Molecular modelling and energy-minimisation studies were also performed to understand the stereospecific binding of substrates to the active site of CRL. The docking of the substrate S(+) ibuprofen to the active site of CRL was performed based on the three-dimensional structure of CRL (PDB entry 1CRL). The results show that only the active S(+) enantiomer of ibuprofen is able to form direct contacts with thereactive hydroxyl group (Ser209) and imidazole base (His449) at the activesite. whereas with the R enantiomer the functional group COOH points away from the (His449) base of CRL. This is in accordance with experimental results which show that the stereospecifity of CRL is towards S(+) ibuprofen.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 25/11/20 alle ore 18:38:19