Transition Metal-Free Reduction of Activated Alkenes Using a Living Microorganism

被引:15
作者
Brewster, Richard C. [1 ]
Suitor, Jack T. [1 ]
Bennett, Adam W. [2 ]
Wallace, Stephen [1 ]
机构
[1] Univ Edinburgh, Inst Quantitat Biol Biochem & Biotechnol, Sch Biol Sci, Kings Bldg,Alexander Crum Brown Rd, Edinburgh EH9 3FF, Midlothian, Scotland
[2] Univ Edinburgh, Sch Chem, Joseph Black Bldg,David Brewster Rd,Kings Bldg, Edinburgh EH9 3FJ, Midlothian, Scotland
基金
英国惠康基金;
关键词
biocatalysis; biotechnology; biotransformation; green chemistry; reduction; ESCHERICHIA-COLI; 5-AMINOLEVULINIC ACID; PHOTODYNAMIC THERAPY; BIOCATALYTIC REDUCTION; HYDROGENATION; EXPRESSION; CELLS;
D O I
10.1002/anie.201903973
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Microorganisms can be programmed to perform chemical synthesis via metabolic engineering. However, despite an increasing interest in the use of de novo metabolic pathways and designer whole-cells for small molecule synthesis, the inherent synthetic capabilities of native microorganisms remain underexplored. Herein, we report the use of unmodified E. coli BL21(DE3) cells for the reduction of keto-acrylic compounds and apply this whole-cell biotransformation to the synthesis of aminolevulinic acid from a lignin-derived feedstock. The reduction reaction is rapid, chemo-, and enantioselective, occurs under mild conditions (37 degrees C, aqueous media), and requires no toxic transition metals or external reductants. This study demonstrates the remarkable promiscuity of central metabolism in bacterial cells and how these processes can be leveraged for synthetic chemistry without the need for genetic manipulation.
引用
收藏
页码:12409 / 12414
页数:6
相关论文
共 41 条
[1]  
[Anonymous], 2019, CHEM WAS USED PREDIC
[2]  
Becker J., 2015, ANGEW CHEM, V127, P3383, DOI [10.1002/ange.201409033, DOI 10.1002/ANGE.201409033]
[3]   Advanced Biotechnology: Metabolically Engineered Cells for the Bio-Based Production of Chemicals and Fuels, Materials, and Health-Care Products [J].
Becker, Judith ;
Wittmann, Christoph .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (11) :3328-3350
[4]   Involvement of rpoS in the survival of Escherichia coli in the viable but non-culturable state [J].
Boaretti, M ;
Lleò, MD ;
Bonato, B ;
Signoretto, C ;
Canepari, P .
ENVIRONMENTAL MICROBIOLOGY, 2003, 5 (10) :986-996
[5]   STATIONARY-PHASE-INDUCIBLE GEARBOX PROMOTERS - DIFFERENTIAL-EFFECTS OF KATF MUTATIONS AND ROLE OF SIGMA-70 [J].
BOHANNON, DE ;
CONNELL, N ;
KEENER, J ;
TORMO, A ;
ESPINOSAURGEL, M ;
ZAMBRANO, MM ;
KOLTER, R .
JOURNAL OF BACTERIOLOGY, 1991, 173 (14) :4482-4492
[6]   A transition-metal-free hydrogenation catalyst: Pore-confined sodium alanate for the hydrogenation of alkynes and alkenes [J].
Bramwell, Peter L. ;
Gao, Jinbao ;
de Waal, Bernd ;
de Jong, Krijn P. ;
Gebbink, Robertus J. M. Klein ;
de Jongh, Petra E. .
JOURNAL OF CATALYSIS, 2016, 344 :129-135
[7]   Substrate-engineering approach to the stereoselective chemo-multienzymatic cascade synthesis of Nicotiana tabacum lactone [J].
Brenna, Elisabetta ;
Gatti, Francesco G. ;
Monti, Daniela ;
Parmeggiani, Fabio ;
Sacchetti, Alessandro ;
Valoti, Jessica .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2015, 114 :77-85
[8]  
Burda E., 2013, ANGEW CHEM, V125, P9493
[9]   Highly Enantioselective Reduction of α-Methylated Nitroalkenes [J].
Burda, Edyta ;
Ress, Tina ;
Winkler, Till ;
Giese, Carolin ;
Kostrov, Xenia ;
Huber, Tobias ;
Hummel, Werner ;
Groeger, Harald .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) :9323-9326
[10]   Phenotypic indications of FtsZ inhibition in hok/sok-induced bacterial growth changes and stress response [J].
Chukwudi, Chinwe Uzoma ;
Good, Liam .
MICROBIAL PATHOGENESIS, 2018, 114 :393-401