Enantioselective reduction and deracemisation using the non-conventional yeast Pichia glucozyma in water/organic solvent biphasic systems: preparation of (S)-1,2-diaryl-2-hydroxyethanones (benzoins)

被引：33

作者：

Caterina Fragnelli, Maria ^{[1
,2
]}

Hoyos, Pilar ^{[1
]}

Romano, Diego ^{[2
]}

Gandolfi, Raffaela ^{[3
]}

Alcantara, Andres R. ^{[1
]}

Molinari, Francesco ^{[2
]}

机构：

[1] Univ Complutense Madrid, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain

[2] Univ Milan, Dipartimento Sci & Tecnol Alimentari & Microbiol, I-20133 Milan, Italy

[3] Univ Milan, Dipartimento Sci Mol Applicate Biosistemi, I-20133 Milan, Italy

来源：

TETRAHEDRON | 2012年 / 68卷 / 02期

关键词：

Benzoin; Deracemisation; Pichia glucozyma; Benzil; Dehydrogenase; Stereoselective reduction; Two-liquid-phase system; DYNAMIC KINETIC RESOLUTION; ALPHA-HYDROXY KETONES; WHOLE CELLS; CHEMOSELECTIVE REDUCTION; BAKERS-YEAST; CONDENSATION; BENZIL; BIOTRANSFORMATIONS; ENZYMES; DERACEMIZATION;

D O I：

10.1016/j.tet.2011.11.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Water/organic solvent two-liquid-phase systems have been successfully applied in the synthesis of enantiomerically pure (S)-benzoin through two different methodologies catalysed by whole cells from the non-conventional yeast Pichia glucozyma: the stereoselective monoreduction of benzil and the deracemisation of benzoin. The presence of the organic solvent influences the redox systems implied in the reactions, avoiding the formation of the corresponding diols, increasing the enantioselectivity and allowing the easy isolation of the products in high yields and excellent enantiomeric excesses. The use of both strategies has been extended to the preparation of different chiral benzoin derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：523 / 528

页数：6

共 43 条

[1] Lipase TL®-mediated kinetic resolution of benzoin:: facile synthesis of (1R,2S)-erythro-2-amino-1,2-diphenylethanol
Aoyagi, Y
Agata, N
Shibata, N
Horiguchi, M
Williams, RM
[J]. TETRAHEDRON LETTERS, 2000, 41 (52) : 10159 - 10162
[2] Solvent applications of 2-methyltetrahydrofuran in organometallic and biphasic reactions
Aycock, David F.
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (01) : 156 - 159
[3] Bag S, 2006, J CHEM RES-S, P267
[4] Optically active cyclobutanone chemistry:: Synthesis of (-)-cyclobut-A and (±)-3′-epi-cyclobut-A
Brown, B
Hegedus, LS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) : 8012 - 8018
[5] Biotransformation in organic media by enzymes and whole cells
Cabral, JMS
Aires-Barros, MR
Pinheiro, H
Prazeres, DMF
[J]. JOURNAL OF BIOTECHNOLOGY, 1997, 59 (1-2) : 133 - 143
[6] Microbial cells as catalysts for stereoselective red-ox reactions
Carballeira, J. D.
Quezada, M. A.
Hoyos, P.
Simeo, Y.
Hernaiz, M. J.
Alcantara, A. R.
Sinisterra, J. V.
[J]. BIOTECHNOLOGY ADVANCES, 2009, 27 (06) : 686 - 714
[7] Synthesis and photoreactivity of 4,5-dithienyl[1,3]dithiol-2-ones
Celli, AM
Donati, D
Ponticelli, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) : 7115 - 7118
[8] Chevenert R., 1988, CHEM LETT, P1191
[9] Extractive biocatalysis: a powerful tool in selectivity control in yeast biotransformations
D'Arrigo, P
Fuganti, C
Fantoni, GP
Servi, S
[J]. TETRAHEDRON, 1998, 54 (49) : 15017 - 15026
[10] Enzymatic reduction of ketones in "micro-aqueous" media catalyzed by ADH-A from Rhodococcus ruber
de Gonzalo, Gonzalo
Lavandera, Ivan
Faber, Kurt
Kroutil, Wolfgang
[J]. ORGANIC LETTERS, 2007, 9 (11) : 2163 - 2166

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