Biotransformation of aromatic ketones and ketoesters with the non-conventional yeast Pichia glucozyma

被引：23

作者：

Contente, Martina Letizia ^{[1
]}

Molinari, Francesco ^{[1
]}

Zambelli, Paolo ^{[1
]}

De Vitis, Valerio ^{[1
]}

Gandolfi, Raffaella ^{[2
]}

Pinto, Andrea ^{[2
]}

Romano, Diego ^{[1
]}

机构：

[1] Univ Milan, Dept Food Environm & Nutr Sci DEFENS, I-20133 Milan, Italy

[2] Univ Milan, Dept Pharmaceut Sci DISFARM, I-20133 Milan, Italy

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 51期

关键词：

Aromatic ketones; Aromatic ketoesters; Reduction; Enantioselective; Ketoreductase; Esterase; STEREOSELECTIVE REDUCTION; REDOX REACTIONS; ESTERS; HYDROGENATION; BIOREDUCTION; ALCOHOLS; CHAIN; ACID;

D O I：

10.1016/j.tetlet.2014.10.133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The non-conventional yeast Pichia glucozyma CBS 5766 has been used for the biotransformation of different aromatic ketones and ketoesters. The growth and biotransformation conditions were optimised for the reduction of acetophenone and under optimised conditions, propiophenone, butyrophenone and valerophenone were reduced to the corresponding (S)-alcohols with high yields and enantioselectivity. Ketoreductase(s) of Pichia glucozyma showed high catalytic activities also towards aromatic beta- and gamma-ketoesters, being often competitive with esterase(s). These concurrent activities allowed for the preparation of hydroxyesters, hydroxyacids and lactones often in a very selective manner. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：7051 / 7053

页数：3

共 28 条

[21] Chelation-controlled highly diastereoselective catalytic hydrogenation of γ-hydroxy-α-methylenecarboxylic acid esters [J].

Nagano, H ;

Yokota, M ;

Iwazaki, Y .

TETRAHEDRON LETTERS, 2004, 45 (15) :3035-3037

[22]

Pàmies O, 2002, ADV SYNTH CATAL, V344, P947, DOI 10.1002/1615-4169(200210)344:9<947::AID-ADSC947>3.0.CO

[23]

2-Z

[24] Enantioselective hydrogenation of β-keto esters using chiral diphosphine-ruthenium complexes:: Optimization for academic and industrial purposes and synthetic applications [J].

Ratovelomanana-Vidal, V ;

Girard, C ;

Touati, R ;

Tranchier, JP ;

Ben Hassine, B ;

Genêt, JP .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :261-274

[25] Chemo- and biocatalytic strategies to obtain phenylisoserine, a lateral chain of Taxol by asymmetric reduction [J].

Rimoldi, Isabella ;

Pellizzoni, Michela ;

Facchetti, Giorgio ;

Molinari, Francesco ;

Zerla, Daniele ;

Gandolfi, Raffaella .

TETRAHEDRON-ASYMMETRY, 2011, 22 (24) :2110-2116

[26] 3-(Hydroxy(phenyl)methyl)azetidin-2-ones obtained via catalytic asymmetric hydrogenation or by biotransformation [J].

Rimoldi, Isabella ;

Cesarotti, Edoardo ;

Zerla, Daniele ;

Molinari, Francesco ;

Albanese, Domenico ;

Castellano, Carlo ;

Gandolfi, Raffaella .

TETRAHEDRON-ASYMMETRY, 2011, 22 (05) :597-602

[27] Enzymatic hydrolysis of capsaicins for the production of vanillylamine using ECB deacylase from Actinoplanes utahensis [J].

Romano, Diego ;

Gandolfi, Raffaella ;

Guglielmetti, Simone ;

Molinari, Francesco .

FOOD CHEMISTRY, 2011, 124 (03) :1096-1098

[28] Highly Enantioselective Intermolecular Stetter Reaction of Simple Acrylates: Synthesis of a-Chiral ?-Ketoesters [J].

Wurz, Nathalie E. ;

Daniliuc, Constantin G. ;

Glorius, Frank .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (51) :16297-16301

← 1 2 3 →