Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways*.
Acetophenones
/ chemistry
Agrocybe
/ enzymology
Alcohol Dehydrogenase
/ chemistry
Benzene Derivatives
/ chemistry
Catalysis
Light
Mixed Function Oxygenases
/ chemistry
Molecular Structure
Nitriles
/ chemistry
Oxidation-Reduction
Phenylethyl Alcohol
/ chemistry
Photochemical Processes
Rhodococcus
/ enzymology
Stereoisomerism
C−H activation
carbon nitrides
chromoselectivity
photobiocatalysis
unspecific peroxygenases
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
22 03 2021
22 03 2021
Historique:
received:
05
01
2021
pubmed:
3
2
2021
medline:
15
7
2021
entrez:
2
2
2021
Statut:
ppublish
Résumé
Controlling the selectivity of a chemical reaction with external stimuli is common in thermal processes, but rare in visible-light photocatalysis. Here we show that the redox potential of a carbon nitride photocatalyst (CN-OA-m) can be tuned by changing the irradiation wavelength to generate electron holes with different oxidation potentials. This tuning was the key to realizing photo-chemo-enzymatic cascades that give either the (S)- or the (R)-enantiomer of phenylethanol. In combination with an unspecific peroxygenase from Agrocybe aegerita, green light irradiation of CN-OA-m led to the enantioselective hydroxylation of ethylbenzene to (R)-1-phenylethanol (99 % ee). In contrast, blue light irradiation triggered the photocatalytic oxidation of ethylbenzene to acetophenone, which in turn was enantioselectively reduced with an alcohol dehydrogenase from Rhodococcus ruber to form (S)-1-phenylethanol (93 % ee).
Identifiants
pubmed: 33529432
doi: 10.1002/anie.202100164
pmc: PMC8048449
doi:
Substances chimiques
Acetophenones
0
Benzene Derivatives
0
Nitriles
0
cyanogen
534Q0F66RK
Mixed Function Oxygenases
EC 1.-
Alcohol Dehydrogenase
EC 1.1.1.1
peroxygenase
EC 1.14.-
ethylbenzene
L5I45M5G0O
Phenylethyl Alcohol
ML9LGA7468
acetophenone
RK493WHV10
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
6965-6969Informations de copyright
© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
Nat Catal. 2018 Jan;1(1):55-62
pubmed: 29430568
Angew Chem Int Ed Engl. 2016 Jan 11;55(2):798-801
pubmed: 26607550
Angew Chem Int Ed Engl. 2011 Mar 7;50(11):2450-94
pubmed: 21365719
ACS Catal. 2019 Feb 1;9(2):890-894
pubmed: 30775065
Nat Commun. 2019 Jun 14;10(1):2634
pubmed: 31201327
Chem Rev. 2016 Jun 22;116(12):7159-329
pubmed: 27199146
Org Lett. 2021 Jan 15;23(2):514-518
pubmed: 33400534
Angew Chem Int Ed Engl. 2019 Jul 8;58(28):9575-9580
pubmed: 31050132
Angew Chem Int Ed Engl. 2016 Jun 27;55(27):7806-10
pubmed: 26953562
ACS Cent Sci. 2021 Jan 27;7(1):55-71
pubmed: 33532569
Appl Environ Microbiol. 2014 Jun;80(11):3496-507
pubmed: 24682297
Curr Opin Chem Biol. 2017 Apr;37:1-9
pubmed: 27992798
Angew Chem Int Ed Engl. 2016 Jun 27;55(27):7676-9
pubmed: 27198967
Angew Chem Int Ed Engl. 2017 Nov 27;56(48):15451-15455
pubmed: 28994504
BMC Evol Biol. 2019 Mar 13;19(1):76
pubmed: 30866798
Angew Chem Int Ed Engl. 2002 Mar 15;41(6):1014-7
pubmed: 12491297
Chem Soc Rev. 2018 Aug 28;47(17):6603-6743
pubmed: 30033454
Chem Rev. 1997 Oct 1;97(6):2063-2192
pubmed: 11848898
Chem Commun (Camb). 2006 Jun 14;(22):2402-4
pubmed: 16733594
Curr Opin Chem Biol. 2014 Apr;19:116-25
pubmed: 24607599
Angew Chem Int Ed Engl. 2019 Nov 11;58(46):16490-16494
pubmed: 31465617
Angew Chem Int Ed Engl. 2017 Oct 16;56(43):13445-13449
pubmed: 28845919
Angew Chem Int Ed Engl. 2019 Jun 3;58(23):7873-7877
pubmed: 30945422
Acc Chem Res. 2017 Mar 21;50(3):465-471
pubmed: 28945402
Angew Chem Int Ed Engl. 2021 Mar 22;60(13):6965-6969
pubmed: 33529432
Angew Chem Int Ed Engl. 2011 Nov 4;50(45):10716-9
pubmed: 21922621
Photochem Photobiol Sci. 2019 Sep 11;18(9):2094-2101
pubmed: 30693928
Enzyme Microb Technol. 2015 Jun;73-74:29-33
pubmed: 26002501
Angew Chem Int Ed Engl. 2014 Dec 1;53(49):13454-9
pubmed: 25293501
Biotechnol Adv. 2020 Aug 19;:107615
pubmed: 32827669