Stereoselective Biotransformations of Cyclic Imines in Recombinant Cells of Synechocystis sp. PCC 6803

被引：32

作者：

Buechsenschuetz, Hanna C. ^{[1
]}

Vidimce-Risteski, Viktorija ^{[2
]}

Eggbauer, Bettina ^{[1
]}

Schmidt, Sandy ^{[1
]}

Winkler, Christoph K. ^{[2
,3
]}

Schrittwieser, Joerg H. ^{[3
]}

Kroutil, Wolfgang ^{[2
,3
]}

Kourist, Robert ^{[1
,2
]}

机构：

[1] Graz Univ Technol, Inst Mol Biotechnol, NAWI Graz, BioTechMe, Petersgasse 14, A-8010 Graz, Austria

[2] Austrian Ctr Ind Biotechnol Acib GmbH, Krenngasse 37, A-8010 Graz, Austria

[3] Karl Franzens Univ Graz, Inst Chem Organ & Bioorgan Chem, NAWI Graz, BioTechMed Graz, Heinrichstr 28-2, A-8010 Graz, Austria

来源：

CHEMCATCHEM | 2020年 / 12卷 / 03期

基金：

奥地利科学基金会;

关键词：

biotechnology; enzyme catalysis; photobiocatalysis; photosynthesis; imine reductase; MONOTERPENE HYDROCARBONS PRODUCTION; ASYMMETRIC REDUCTION; REDUCTASES; EXPRESSION; DISCOVERY; OXIDATION;

D O I：

10.1002/cctc.201901592

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Light-driven biotransformations in recombinant cyanobacteria allow to employ photosynthetic water-splitting for cofactor-regeneration and thus, to save the use of organic electron donors. The genes of three recombinant imine reductases (IREDs) were expressed in the cyanobacterium Synechocystis sp. PCC 6803 and eight cyclic imine substrates were screened in whole-cell biotransformations. While initial reactions showed low to moderate rates, optimization of the reaction conditions in combination with promoter engineering allowed to alleviate toxicity effects and achieve full conversion of prochiral imines with initial rates of up to 6.3 mM h(-1). The high specific activity of up to 22 U g(CDW)(-1) demonstrates that recombinant cyanobacteria can provide large amounts of NADPH during whole cell reactions. The excellent optical purity of the products with up to >99 %ee underlines the usefulness of cyanobacteria for the stereoselective synthesis of amines.

引用

页码：726 / 730

页数：5

共 35 条

[1] Synthesis of N-heterocycles from diamines via H2-driven NADPH recycling in the presence of O2 [J].

Al-Shameri, Ammar ;

Borlinghaus, Niels ;

Weinmann, Leonie ;

Scheller, Philipp N. ;

Nestl, Bettina M. ;

Lauterbach, Lars .

GREEN CHEMISTRY, 2019, 21 (06) :1396-1400

[2] Hydrogen-Driven Cofactor Regeneration for Stereoselective Whole-Cell C=C Bond Reduction in Cupriavidus necator [J].

Assil-Companioni, Leen ;

Schmidt, Sandy ;

Heidinger, Petra ;

Schwab, Helmut ;

Kourist, Robert .

CHEMSUSCHEM, 2019, 12 (11) :2361-2365

[3] Photosynthetic production of enantioselective biocatalysts [J].

Bartsch, Maik ;

Gassmeyer, Sarah K. ;

Koeninger, Katharina ;

Igarashi, Kosuke ;

Liauw, Pasqual ;

Dyczmons-Nowaczyk, Nina ;

Miyamoto, Kenji ;

Nowaczyk, Marcm ;

Kourist, Robert .

MICROBIAL CELL FACTORIES, 2015, 14

[4] Enzymatic Oxyfunctionalization Driven by Photosynthetic Water-Splitting in the Cyanobacterium Synechocystis sp PCC 6803 [J].

Boehmer, Stefanie ;

Koeninger, Katharina ;

Gomez-Baraibar, Alvaro ;

Bojarra, Samiro ;

Muegge, Carolin ;

Schmidt, Sandy ;

Nowaczyk, Marc M. ;

Kourist, Robert .

CATALYSTS, 2017, 7 (08)

[5] Engineering the third wave of biocatalysis [J].

Bornscheuer, U. T. ;

Huisman, G. W. ;

Kazlauskas, R. J. ;

Lutz, S. ;

Moore, J. C. ;

Robins, K. .

NATURE, 2012, 485 (7397) :185-194

[6] Imine Reductases, Reductive Aminases, and Amine Oxidases for the Synthesis of Chiral Amines: Discovery, Characterization, and Synthetic Applications [J].

Cosgrove, Sebastian C. ;

Brzezniak, Agata ;

France, Scott P. ;

Ramsden, Jeremy I. ;

Mangas-Sanchez, Juan ;

Montgomery, Sarah L. ;

Heath, Rachel S. ;

Turner, Nicholas J. .

ENZYMES IN SYNTHETIC BIOLOGY, 2018, 608 :131-149

[7]

Englund E, 2016, SCI REP, V6, P1

[8] A phycocyanin • phellandrene synthase fusion enhances recombinant protein expression and β-phellandrene (monoterpene) hydrocarbons production in Synechocystis (cyanobacteria) [J].

Formighieri, Cinzia ;

Melis, Anastasios .

METABOLIC ENGINEERING, 2015, 32 :116-124

[9] Regulation of β-phellandrene synthase gene expression, recombinant protein accumulation, and monoterpene hydrocarbons production in Synechocystis transformants [J].

Formighieri, Cinzia ;

Melis, Anastasios .

PLANTA, 2014, 240 (02) :309-324

[10] Biocatalytic Approaches to the Synthesis of Enantiomerically Pure Chiral Amines [J].

Ghislieri, Diego ;

Turner, Nicholas J. .

TOPICS IN CATALYSIS, 2014, 57 (05) :284-300

← 1 2 3 4 →