Synthesis of Enantiopure Sulfoxides by Concurrent Photocatalytic Oxidation and Biocatalytic Reduction.
Biocatalysis
Deracemization
Methionine Sulfoxide Reductases
Photocatalysis
Sulfoxides
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:
19 04 2022
19 04 2022
Historique:
received:
15
12
2021
pubmed:
22
2
2022
medline:
15
4
2022
entrez:
21
2
2022
Statut:
ppublish
Résumé
The concurrent operation of chemical and biocatalytic reactions in one pot is still a challenging task, and, in particular for chemical photocatalysts, examples besides simple cofactor recycling systems are rare. However, especially due to the complementary chemistry that the two fields of catalysis promote, their combination in one pot has the potential to unlock intriguing, unprecedented overall reactivities. Herein we demonstrate a concurrent biocatalytic reduction and photocatalytic oxidation process. Specifically, the enantioselective biocatalytic sulfoxide reduction using (S)-selective methionine sulfoxide reductases was coupled to an unselective light-dependent sulfoxidation. Protochlorophyllide was established as a new green photocatalyst for the sulfoxidation. Overall, a cyclic deracemization process to produce nonracemic sulfoxides was achieved and the target compounds were obtained with excellent conversions (up to 91 %) and superb optical purity (>99 % ee).
Identifiants
pubmed: 35188997
doi: 10.1002/anie.202117103
pmc: PMC9310851
doi:
Substances chimiques
Sulfoxides
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202117103Informations de copyright
© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
Photochem Photobiol. 2004 Jan;79(1):62-7
pubmed: 14974717
Chem Sci. 2018 May 17;9(22):5052-5056
pubmed: 29938035
Anal Chem. 2018 Aug 21;90(16):9997-10000
pubmed: 30045620
Nature. 2016 Dec 14;540(7633):414-417
pubmed: 27974767
Angew Chem Int Ed Engl. 2018 Jul 2;57(27):7958-7985
pubmed: 29194901
Biochemistry. 2003 Jan 21;42(2):523-8
pubmed: 12525180
Angew Chem Int Ed Engl. 2003 Feb 3;42(5):577-9
pubmed: 12569495
ACS Cent Sci. 2021 Jan 27;7(1):55-71
pubmed: 33532569
Chembiochem. 2021 Apr 6;22(7):1232-1242
pubmed: 33242357
Nat Chem. 2010 Jul;2(7):527-32
pubmed: 20571569
Prog Biophys Mol Biol. 1997;68(2-3):121-44
pubmed: 9652170
Bioengineering (Basel). 2018 Aug 01;5(3):
pubmed: 30071637
Chemistry. 2014 Jan 20;20(4):966-9
pubmed: 24375662
Drug Metab Dispos. 2011 Jun;39(6):1014-21
pubmed: 21383205
Curr Opin Green Sustain Chem. 2021 Mar 10;30:100476
pubmed: 34141957
J Biotechnol. 2012 Aug 31;160(3-4):189-94
pubmed: 22475681
Chembiochem. 2021 Mar 2;22(5):790-806
pubmed: 32961020
Front Chem. 2019 Nov 29;7:829
pubmed: 31850317
Science. 2020 Aug 28;369(6507):1113-1118
pubmed: 32855338
J Biol Chem. 1992 Aug 5;267(22):15549-51
pubmed: 1386361
Chem Soc Rev. 2021 Dec 13;50(24):13449-13466
pubmed: 34734949
Curr Opin Biotechnol. 2003 Aug;14(4):407-13
pubmed: 12943850
Angew Chem Int Ed Engl. 2018 Jul 26;57(31):9849-9852
pubmed: 29888843
Atmos Chem Phys. 2012 May 3;12(5):11317-11350
pubmed: 23393494
Angew Chem Int Ed Engl. 2018 May 14;57(20):5803-5807
pubmed: 29533509
Nature. 2018 Aug;560(7718):355-359
pubmed: 30111790
RSC Chem Biol. 2021 Jun 1;2(4):958-989
pubmed: 34458820
Nature. 2018 Jan 31;554(7690):41-49
pubmed: 29388950
Chem Commun (Camb). 2019 Aug 27;55(70):10480-10483
pubmed: 31411608
Angew Chem Int Ed Engl. 2022 Apr 19;61(17):e202117103
pubmed: 35188997
Angew Chem Int Ed Engl. 2021 Mar 22;60(13):7041-7045
pubmed: 33373075
Chem Rev. 2018 Jan 10;118(1):270-348
pubmed: 28481088
Chem Soc Rev. 2018 Feb 21;47(4):1307-1350
pubmed: 29271432
Chem Sci. 2020 Feb 13;11(10):2587-2605
pubmed: 32206264
Org Biomol Chem. 2019 Aug 14;17(30):7144-7149
pubmed: 31328217
Chem Rev. 2003 Sep;103(9):3651-705
pubmed: 12964880
Angew Chem Int Ed Engl. 2021 Mar 22;60(13):6965-6969
pubmed: 33529432
Angew Chem Int Ed Engl. 2018 Oct 15;57(42):13825-13828
pubmed: 30062834
Chem Rev. 2013 Jul 10;113(7):5322-63
pubmed: 23509883
Org Biomol Chem. 2019 Mar 27;17(13):3381-3388
pubmed: 30860233
Sci Rep. 2018 Feb 2;8(1):2205
pubmed: 29396475
Angew Chem Int Ed Engl. 2021 Jan 4;60(1):88-119
pubmed: 32558088
Cryst Growth Des. 2017 Aug 2;17(8):4454-4457
pubmed: 28794692
Chem Commun (Camb). 2010 Nov 14;46(42):8046-8
pubmed: 20871888
Angew Chem Int Ed Engl. 2018 Aug 6;57(32):10034-10072
pubmed: 29457971
European J Org Chem. 2019 Jan 10;2019(1):80-84
pubmed: 31007570
Biotechnol Bioeng. 2001 Apr 5;73(1):80-2
pubmed: 11255155