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

详细信息    查看全文

• 作者：Martina Letizia Contente ; Immacolata Serra…
• 关键词：Ketoreductase ; Carbonyl reductase ; Pichia glucozyma ; Enantioselective reduction ; Biocatalysis ; Stereoselective
• 刊名：Applied Microbiology and Biotechnology
• 出版年：2016
• 出版时间：January 2016
• 年：2016
• 卷：100
• 期：1
• 页码：193-201
• 全文大小：413 KB
• 参考文献：Baerga-Ortiz A, Popovic B, Siskos AP, O’Hare HM, Spiteller D, Williams MG, Campillo N, Spencer JB, Leadlay PF (2006) Directed mutagenesis alters the stereochemistry of catalysis by isolated ketoreductase domains from the erythromycin polyketide synthase. Chem Biol 13:277–285. doi:10.​1016/​j.​chembiol.​2006.​01.​004 PubMed CrossRef
  Bechtold M, Brenna E, Femmer C, Gatti FG, Panke S, Parmeggiani F, Sacchetti A (2012) 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. Org Process Res Dev 16(2):269–276CrossRef
  Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248–254PubMed CrossRef
  Contente ML, Molinari F, Zambelli P, De Vitis V, Gandolfi R, Pinto A, Romano D (2014) Biotransformation of aromatic ketones and ketoesters with the non-conventional yeast Pichia glucozyma. Tetrahedron Lett 55(51):7051–7053CrossRef
  Contente ML, Zambelli P, Galafassi S, Tamborini L, Pinto A, Conti P, Molinari F, Romano D (2015) A new chemoenzymatic approach to the synthesis of Latanoprost and Bimatoprost. J Mol Catal B Enzym. doi:10.​1016/​j.​molcatb.​2014.​05.​022
  Eberini I, Fantucci P, Rocco AG, Gianazza E, Galluccio L, Maggioni D, Ben ID, Galliano M, Mazzitello R, Gaiji N, Beringhelli T (2006) Computational and experimental approaches for assessing the interactions between the model calycin β-lactoglobulin and two antibacterial fluoroquinolones. Proteins 65:555–567. doi:10.​1002/​prot.​21109 PubMed CrossRef
  Forzato C, Gandolfi R, Molinari F, Nitti P, Pitacco G, Valentin E (2001) Microbial bioreductions of γ- and δ-ketoacids and their esters. Tetrahedron 12:1039–1046. doi:10.​1016/​S0957-4166(01)00184-7 CrossRef
  Fragnelli MC, Hoyos P, Romano D, Gandolfi R, Alcántara AR, Molinari F (2012) 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). Tetrahedron 68:523–528. doi:10.​1016/​j.​tet.​2011.​11.​014 CrossRef
  Gandolfi R, Cesarotti E, Molinari F, Romano D (2009) Asymmetric reductions of ethyl 2-(benzamidomethyl)-3-oxobutanoate by yeasts. Tetrahedron 20:411–414. doi:10.​1016/​j.​tetasy.​2009.​02.​023 CrossRef
  Haberland J, Kriegesmann A, Wolfram E, Hummel W, Liese A (2002) Diastereoselective synthesis of optically active (2R,5R)- hexanediol. Appl Microbiol Biotechnol 58:595–599PubMed CrossRef
  Hall M, Bommarius AS (2011) Enantioenriched compounds via enzyme-catalyzed redox reactions. Chem Rev 111:4088–4110. doi:10.​1021/​cr200013n PubMed CrossRef
  Hollmann F, Arends IWCE, Holtmann D (2011) Enzymatic reductions for the chemist. Green Chem 13:2285–2314CrossRef
  Hoyos P, Sansottera G, Fernández M, Molinari F, Sinisterra JV, Alcántara AR (2008) Enantioselective monoreduction of different 1,2-diaryl-1,2-diketones catalysed by lyophilised whole cells from Pichia glucozyma. Tetrahedron 64:7929–7936. doi:10.​1016/​j.​tet.​2008.​06.​019 CrossRef
  Huisman GW, Liang J, Krebber A (2010) Practical chiral alcohol manufacture using ketoreductases. Current Opinion in Chemical Biology 14:122–129. doi:10.​1016/​j.​cbpa.​2009.​12.​003 PubMed CrossRef
  Husain SM, Stillger T, Dünkelmann P, Lodige M, Walter L, Breitling E, Pohl M, Bürchner M, Krossing I, Müller M, Romano D, Molinari F (2011) Stereoselective reduction of 2-hydroxy ketones towards syn- and anti-1,2-diols. Adv Synth Catal 353:2359–2362. doi:10.​1002/​adcs.​201100150 CrossRef
  Johanson T, Katz M, Gorwa-Grauslund MF (2005) Strain engineering for stereoselective bioreduction of dicarbonyl compounds by yeast reductases. FEMS Yeast Res 5:513–525. doi:10.​1016/​j.​femsyr.​2004.​12.​006 PubMed CrossRef
  Lavandera I, Kern A, Ferreira-Silva B, Glieder A, de Wildeman S, Kroutil W (2008) Stereoselective bioreduction of bulky-bulky ketones by a novel ADH from Ralstonia sp. J Org Chem 73:6003–6005. doi:10.​1021/​jo800849d PubMed CrossRef
  Li H, Zhu D, Hua L, Biehl ER (2009) Enantioselective reduction of diaryl ketones catalyzed by a carbonyl reductase from Sporobolomyces salmonicolor and its mutant enzymes. Adv Synth Catal 351:583–588. doi:10.​1002/​adsc.​200900045 CrossRef
  Liang J, Lalonde J, Borup B, Mitchell V, Mundorff E, Trinh N, Kochrekar DA, Cherat RN, Pai GG (2010) Development of a biocatalytic process as an alternative to the (−)-DIP-Cl-mediated asymmetric reduction of a key intermediate of Montelukast. Org Process Res Dev 14:193–198. doi:10.​1021/​op900272d CrossRef
  Maruyama R, Nishizawa M, Itoi Y, Ito S, Inoue M (2002) The enzymes with benzil reductase activity conserved from bacteria to mammals. J Biotechnol 94:157–169. doi:10.​1016/​S0168-1656(01)00426-6 PubMed CrossRef
  O’Hare HM, Baerga-Ortiz A, Popovic B, Spencer JB, Leadlay PF (2006) High-throughput mutagenesis to evaluate models of stereochemical control in ketoreductase domains from the Erythromycin polyketide synthase. Chem Biol 13:287–296. doi:10.​1016/​j.​chembiol.​2006.​01.​003 PubMed CrossRef
  Rimoldi I, Cesarotti E, Zerla D, Molinari F, Albanese D, Castellano C, Gandolfi R (2011a) Chemo- and biocatalytic strategies to obtain phenylisoserine, a lateral chain of Taxol by asymmetric reduction. Tetrahedron: Asymmetry 22:597–602. doi:10.​1016/​j.​tetasy.​2011.​11.​017 CrossRef
  Rimoldi I, Pellizzoni M, Facchetti G, Molinari F, Zerla D, Gandolfi R (2011b) 3-(Hydroxy(phenyl)methyl)azetidin-2-ones obtained via catalytic asymmetric hydrogenation or by biotransformation. Tetrahedron: Asymmetry 22:2110–2116. doi:10.​1016/​j.​tetasy.​2011.​03.​007 CrossRef
  Rodríguez C, Borzęcka W, Sattler JH, Kroutil W, Lavandera I, Gotor V (2014) Steric vs. electronic effects in the Lactobacillus brevis ADH-catalyzed bioreduction of ketones. Org Biomol Chem 12:673–681. doi:10.​1039/​C3OB42057D PubMed CrossRef
  Sambrook J, Russell DW (2001) Molecular Cloning: A Laboratory Manual, 3rd edn. Cold Spring Harbor Laboratory, New York
  Stampfer W, Edegger K, Kosjek B, Faber K, Kroutil W (2004) Simple biocatalytic access to enantiopure (S)-1-heteroarylethanols employing a microbial hydrogen transfer reaction. Adv Synth Catal 346:57–62CrossRef
  Truppo MD, Pollard D, Devine P (2007) Enzyme-Catalyzed enantioselective diaryl ketone reductions. Org Lett 9:335–338. doi:10.​1021/​ol0627909 PubMed CrossRef
  Zhu D, Yang Y, Hua L (2006) Stereoselective enzymatic synthesis of chiral alcohols with the use of a carbonyl reductase from Candida magnoliae with anti-prelog enantioselectivity. J Org Chem 71:4202–4205PubMed CrossRef
  Zhu D, Yang Y, Majkowicz S, Pan T (2008) Inverting the enantioselectivity of a carbonyl reductase via substrate−enzyme docking-guided point mutation. Org Lett 10:525–528. doi:10.​1021/​ol702638j PubMed CrossRef
  
• 作者单位：Martina Letizia Contente (1)
  Immacolata Serra (1)
  Marta Brambilla (1)
  Ivano Eberini (1)
  Elisabetta Gianazza (2)
  Valerio De Vitis (1)
  Francesco Molinari (1)
  Paolo Zambelli (2)
  Diego Romano (1)
  
  1. Department of Food, Environmental and Nutritional Sciences (DeFENS), University of Milan, Via Mangiagalli 25, 20133, Milan, Italy
  2. Department of Pharmacological and Biomolecular Sciences (DiSFeB), University of Milan, Via Balzaretti 9, 20133, Milano, Italy
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Biotechnology
  Microbiology
  Microbial Genetics and Genomics
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1432-0614

文摘

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.