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Titolo:
Enantioselective oxidation and reduction by Geotrichum candidum
Autore:
Matsuda, T; Harada, T; Nakamura, K;
Indirizzi:
Kyoto Univ, Inst Chem Res, Uji, Kyoto 6110011, Japan Kyoto Univ Uji KyotoJapan 6110011 st Chem Res, Uji, Kyoto 6110011, Japan
Titolo Testata:
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
fascicolo: 7, volume: 59, anno: 2001,
pagine: 659 - 669
SICI:
0037-9980(200107)59:7<659:EOARBG>2.0.ZU;2-S
Fonte:
ISI
Lingua:
JPN
Soggetto:
SUPERCRITICAL CARBON-DIOXIDE; ASYMMETRIC REDUCTION; ORGANIC-SOLVENT; MICROBIAL REDUCTION; GLYCEROL DEHYDROGENASE; ALCOHOL-DEHYDROGENASE; ACETONE POWDER; TRIFLUOROMETHYL KETONES; CHEMOENZYMATIC SYNTHESIS; TRIHALOMETHYL KETONES;
Keywords:
Geotrichum candidum; asymmetric reduction; enantioselective oxidation; deracemization; organic solvent; supercritical carbon dioxide; biocatalysis; fluorine; optically active alcohols; dehydrogenase;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
65
Recensione:
Indirizzi per estratti:
Indirizzo: Matsuda, T Kyoto Univ, Inst Chem Res, Uji, Kyoto 6110011, Japan Kyoto Univ Uji Kyoto Japan 6110011 , Uji, Kyoto 6110011, Japan
Citazione:
T. Matsuda et al., "Enantioselective oxidation and reduction by Geotrichum candidum", J SYN ORG J, 59(7), 2001, pp. 659-669

Abstract

Biocatalyst has been attracted increasing attention for asymmetric synthesis due to the high enantioselectivities and environmentally friendliness. We have been developing methods using a fungus, Geotrichum candidum, which has many enzymes catalyzing the enantioselective oxidation and reduction reactions of non-natural substrates. These enzymes in the resting or dried cells were used in an organic solvent, supercritical carbon dioxide, or aqueous media for oxidation, reduction or deracemization reactions. The usefulness of these methods was also demonstrated in the preparation, on a multi-gram scale, of optically pure alcohols. The effect of fluorine substituents on the enantioselectivity of the reduction using the dried cell was also investigated thoroughly, and it was found that the reduction of trifluoromethyl ketones affords (S)-trifluoromethylcarbinols in excellent ee, whereas the reduction of methyl ketones gives the corresponding alcohols of the opposite configuration in excellent ee. The enzymes in the cells were separated to investigate the origin of different enantioselectivities between the methyl and trifluoromethyl ketones.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 10/04/20 alle ore 02:04:00