Stereoselective reduction of aromatic ketones by a new ketoreductase from Pichia glucozyma

被引：32

作者：

Contente, Martina Letizia ^{[1
]}

Serra, Immacolata ^{[1
]}

Brambilla, Marta ^{[1
]}

Eberini, Ivano ^{[1
]}

Gianazza, Elisabetta ^{[2
]}

De Vitis, Valerio ^{[1
]}

Molinari, Francesco ^{[1
]}

Zambelli, Paolo ^{[2
]}

Romano, Diego ^{[1
]}

机构：

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

[2] Univ Milan, Dept Pharmacol & Biomol Sci DiSFeB, I-20133 Milan, Italy

来源：

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY | 2016年 / 100卷 / 01期

关键词：

Ketoreductase; Carbonyl reductase; Pichia glucozyma; Enantioselective reduction; Biocatalysis; Stereoselective; ERYTHROMYCIN POLYKETIDE SYNTHASE; CARBONYL REDUCTASE; ENANTIOSELECTIVE REDUCTION; ASYMMETRIC REDUCTION; BIOREDUCTION; BIOTRANSFORMATION; MUTAGENESIS; DOMAINS; ENZYMES; ADH;

D O I：

10.1007/s00253-015-6961-y

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

A new NADPH-dependent benzil reductase (KRED1-Pglu) was identified from the genome of the non-conventional yeast Pichia glucozyma CBS 5766 and overexpressed in E. coli. The new protein was characterised and reaction parameters were optimised for the enantioselective reduction of benzil to (S)-benzoin. A thorough study of the substrate range of KRED1-Pglu was conducted; in contrast to most other known ketoreductases, KRED1-Pglu prefers space-demanding substrates, which are often converted with high stereoselectivity. A molecular modelling study was carried out for understanding the structural determinants involved in the stereorecognition experimentally observed and unpredictable on the basis of steric properties of the substrates. As a result, a new useful catalyst was identified, enabling the enantioselective preparation of different aromatic alcohols and hydroxyketones.

引用

页码：193 / 201

页数：9

共 29 条

[1] Directed mutagenesis alters the stereochemistry of catalysis by isolated ketoreductase domains from the erythromycin polyketide synthase [J].

Baerga-Ortiz, A ;

Popovic, B ;

Siskos, AP ;

O'Hare, HM ;

Spiteller, D ;

Williams, MG ;

Campillo, N ;

Spencer, JB ;

Leadlay, PF .

CHEMISTRY & BIOLOGY, 2006, 13 (03) :277-285

[2] Biotechnological Development of a Practical Synthesis of Ethyl (S)-2-Ethoxy-3-(p-methoxyphenyl)propanoate (EEHP): Over 100-Fold Productivity Increase from Yeast Whole Cells to Recombinant Isolated Enzymes [J].

Bechtold, Matthias ;

Brenna, Elisabetta ;

Femmer, Christian ;

Gatti, Francesco G. ;

Panke, Sven ;

Parmeggiani, Fabio ;

Sacchetti, Alessandro .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (02) :269-276

[3]

BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3

[4] 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) [J].

Caterina Fragnelli, Maria ;

Hoyos, Pilar ;

Romano, Diego ;

Gandolfi, Raffaela ;

Alcantara, Andres R. ;

Molinari, Francesco .

TETRAHEDRON, 2012, 68 (02) :523-528

[5] A new chemoenzymatic approach to the synthesis of Latanoprost and Bimatoprost [J].

Contente, Martina Letizia ;

Zambelli, Paolo ;

Galafassi, Silvia ;

Tamborini, Lucia ;

Pinto, Andrea ;

Conti, Paola ;

Molinari, Francesco ;

Romano, Diego .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2015, 114 :7-12

[6] Biotransformation of aromatic ketones and ketoesters with the non-conventional yeast Pichia glucozyma [J].

Contente, Martina Letizia ;

Molinari, Francesco ;

Zambelli, Paolo ;

De Vitis, Valerio ;

Gandolfi, Raffaella ;

Pinto, Andrea ;

Romano, Diego .

TETRAHEDRON LETTERS, 2014, 55 (51) :7051-7053

[7] Computational and experimental approaches for assessing the interactions between the model calycin β-lactoglobulin and two antibacterial fluoroquinolones [J].

Eberini, Ivano ;

Fantucci, Piercarlo ;

Rocco, Alessandro Guerini ;

Gianazza, Elisabetta ;

Galluccio, Lara ;

Maggioni, Daniela ;

Dal Ben, Ilaria ;

Galliano, Monica ;

Mazzitello, Rosalba ;

Gaiji, Noura ;

Beringhelli, Tiziana .

PROTEINS-STRUCTURE FUNCTION AND BIOINFORMATICS, 2006, 65 (03) :555-567

[8] Microbial bioreductions of γ- and δ-ketoacids and their esters [J].

Forzato, C ;

Gandolfi, R ;

Molinari, F ;

Nitti, P ;

Pitacco, G ;

Valentin, E .

TETRAHEDRON-ASYMMETRY, 2001, 12 (07) :1039-1046

[9] Asymmetric reductions of ethyl 2-(benzamidomethyl)-3-oxobutanoate by yeasts [J].

Gandolfi, Raffaella ;

Cesarotti, Edoardo ;

Molinari, Francesco ;

Romano, Diego ;

Rimoldi, Isabella .

TETRAHEDRON-ASYMMETRY, 2009, 20 (04) :411-414

[10] Diastereoselective synthesis of optically active (2R,5R)-hexanediol [J].

Haberland, J ;

Kriegesmann, A ;

Wolfram, E ;

Hummel, W ;

Liese, A .

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2002, 58 (05) :595-599

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