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Whole-Cell-Catalyzed Multiple Regio- And Stereoselective Functionalizations In Cascade Reactions Enabled By Directed Evolution.

Aitao Li, Adriana Ilie, Zhoutong Sun, Richard Lonsdale, Jian-he Xu, Manfred T Reetz
Published 2016 · Medicine, Chemistry
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Biocatalytic cascade reactions using isolated stereoselective enzymes or whole cells in one-pot processes lead to value-added chiral products in a single workup. The concept has been restricted mainly to starting materials and intermediate products that are accepted by the respective wild-type enzymes. In the present study, we exploited directed evolution as a means to create E. coli whole cells for regio- and stereoselective cascade sequences that are not possible using man-made catalysts. The approach is illustrated using P450-BM3 in combination with appropriate alcohol dehydrogenases as catalysts in either two-, three-, or four-step cascade reactions starting from cyclohexane, cyclohexanol, or cyclohexanone, respectively, leading to either (R,R)-, (S,S)-, or meso-cyclohexane-1,2-diol. The one-pot conversion of cyclohexane into (R)- or (S)-2-hydroxycyclohexanone in the absence of ADH is also described.



This paper is referenced by
10.1111/cbdd.13443
Whole-cell biocatalysis platform for gram-scale oxidative dearomatization of phenols.
Summer A Baker Dockrey (2018)
10.1016/j.tibtech.2019.01.001
Cytochrome P450 Monooxygenases in Biotechnology and Synthetic Biology.
Vlada B Urlacher (2019)
10.1021/ACSCATAL.7B01464
Biocatalytic Formal Anti-Markovnikov Hydroamination and Hydration of Aryl Alkenes
Shuke Wu (2017)
10.13345/j.cjb.190221
[Protein engineering: from directed evolution to computational design].
Ge Qu (2019)
10.1039/c7ob00391a
Spatial organization of multi-enzyme biocatalytic cascades.
Maureen B. Quin (2017)
10.1002/IJCH.201700091
Combinatorial Libraries Reloaded[1]
Manfred Theodor Reetz (2018)
10.1002/anie.201800343
Biocatalytic Oxidation Reactions: A Chemist's Perspective
Jiajia Dong (2018)
10.1002/anie.201901491
The Crucial Role of Methodology Development in Directed Evolution of Selective Enzymes.
Ge Qu (2019)
10.1039/c7ob02236k
Hydroxylation of anilides by engineered cytochrome P450BM3.
Jack A. O'Hanlon (2017)
10.1021/acs.chemrev.7b00203
Role of Biocatalysis in Sustainable Chemistry.
Roger A. Sheldon (2018)
10.1002/EJOC.201900904
One‐Pot Two‐Step Chemoenzymatic Cascade for the Synthesis of a Bis‐benzofuran Derivative
Martin Mertens (2019)
10.3390/CATAL6120194
Tandem reactions combining biocatalysts and chemical catalysts for asymmetric synthesis
Yajie Wang (2016)
10.1002/CCTC.201701669
Whole‐Cell Cascade Biotransformations for One‐Pot Multistep Organic Synthesis
Shuke Wu (2018)
10.1002/cbic.201700546
Stabilization of the Reductase Domain in the Catalytically Self-Sufficient Cytochrome P450BM3 by Consensus-Guided Mutagenesis.
Gloria Saab-Rincon (2018)
10.1002/cbic.201800339
Solid-Phase Gene Synthesis for Mutant Library Construction: The Future of Directed Evolution?
Aitao Li (2018)
10.1002/ANGE.201703806
Kaskaden in Kompartimenten: auf dem Weg zu maschinengestützter Biotechnologie
Kersten S. Rabe (2017)
10.1002/CCTC.201801050
Production of β‐Alanine from Fumaric Acid Using a Dual‐Enzyme Cascade
Yuanyuan Qian (2018)
10.1002/cbic.201700562
Methodology Development in Directed Evolution: Exploring Options when Applying Triple-Code Saturation Mutagenesis.
Ge Qu (2018)
10.1186/s40643-019-0290-4
Bacterial cytochrome P450-catalyzed regio- and stereoselective steroid hydroxylation enabled by directed evolution and rational design
Xinpeng Zhang (2020)
10.1002/cctc.201901347
Directed Evolution of P450 Fatty Acid Decarboxylases via High‐Throughput Screening towards Improved Catalytic Activity
Huifang Xu (2020)
10.1002/anie.201804924
Whole-Cell Biotransformation of Benzene to Phenol Catalysed by Intracellular Cytochrome P450BM3 Activated by External Additives.
Masayuki Karasawa (2018)
10.1039/C9GC01802F
Cascade bio-hydroxylation and dehalogenation for one-pot enantioselective synthesis of optically active β-halohydrins from halohydrocarbons
Hai-Bo Cui (2019)
10.1186/s12934-017-0720-y
Cell foundry with high product specificity and catalytic activity for 21-deoxycortisol biotransformation
Shuting Xiong (2017)
10.3390/molecules24183303
Chemical and Biocatalytic Routes to Arbutin †
Hangyu Zhou (2019)
10.13345/j.cjb.170273
[Recent advances in directed evolution].
Ge Qu (2018)
10.1002/anie.201812093
Chemo- and Regioselective Dihydroxylation of Benzene to Hydroquinone Enabled by Engineered Cytochrome P450 Monooxygenase.
Hangyu Zhou (2019)
10.1016/j.tibs.2019.06.006
Engineering Metalloprotein Functions in Designed and Native Scaffolds.
Flavia Nastri (2019)
10.1038/s41467-018-06241-x
Asymmetric assembly of high-value α-functionalized organic acids using a biocatalytic chiral-group-resetting process
Wei Song (2018)
10.1002/ejoc.201901682
Enantiocomplementary C–H Bond Hydroxylation Combining Photo‐Catalysis and Whole‐Cell Biocatalysis in a One‐Pot Cascade Process
Yong-zhen Peng (2020)
10.1002/anie.201710793
Temperature-Directed Biocatalysis for the Sustainable Production of Aromatic Aldehydes or Alcohols.
Jun Ni (2018)
10.1002/CCTC.201700620
One-pot Biocatalytic Double Oxidation of α-Isophorone for the Synthesis of Ketoisophorone
Michele Tavanti (2017)
10.1002/ADSC.201700416
Regio‐ and Stereoselective Oxidation of Styrene Derivatives to Arylalkanoic Acids via One‐Pot Cascade Biotransformations
Shuke Wu (2017)
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