Selective Functionalisation of 5-Methylcytosine by Organic Photoredox Catalysis.
C−H Functionalization
Nucleic Acids
Photocatalysis
Radicals
Reaction Mechanisms
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:
26 06 2023
26 06 2023
Historique:
received:
04
04
2023
medline:
19
6
2023
pubmed:
29
4
2023
entrez:
29
4
2023
Statut:
ppublish
Résumé
The epigenetic modification 5-methylcytosine plays a vital role in development, cell specific gene expression and disease states. The selective chemical modification of the 5-methylcytosine methyl group is challenging. Currently, no such chemistry exists. Direct functionalisation of 5-methylcytosine would improve the detection and study of this epigenetic feature. We report a xanthone-photosensitised process that introduces a 4-pyridine modification at a C(sp
Identifiants
pubmed: 37118885
doi: 10.1002/anie.202304756
doi:
Substances chimiques
5-Methylcytosine
6R795CQT4H
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202304756Subventions
Organisme : Wellcome Trust
ID : 209441/Z/17/Z
Pays : United Kingdom
Organisme : Cancer Research UK
ID : C9681/A29214
Pays : United Kingdom
Organisme : Cancer Research UK
ID : C9545/A19863
Pays : United Kingdom
Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
Phys Chem Chem Phys. 2008 Nov 28;10(44):6615-20
pubmed: 18989472
Nat Biotechnol. 2023 Mar;41(3):344-354
pubmed: 36302989
J Am Chem Soc. 2013 Aug 14;135(32):12122-34
pubmed: 23859263
J Am Chem Soc. 2013 Nov 20;135(46):17494-500
pubmed: 24180320
J Comput Chem. 2011 May;32(7):1456-65
pubmed: 21370243
Nat Commun. 2021 Jan 27;12(1):618
pubmed: 33504799
Phys Rev A Gen Phys. 1988 Sep 15;38(6):3098-3100
pubmed: 9900728
Angew Chem Int Ed Engl. 2021 Sep 20;60(39):21457-21463
pubmed: 34181314
Science. 2011 Nov 25;334(6059):1114-7
pubmed: 22116882
J Am Chem Soc. 2020 Dec 23;142(51):21484-21492
pubmed: 33305571
Nucleic Acids Res. 2012 Jun;40(11):5023-33
pubmed: 22344696
Biochim Biophys Acta Gene Regul Mech. 2019 Mar;1862(3):240-252
pubmed: 30593929
Protein Cell. 2020 Nov;11(11):792-808
pubmed: 32440736
Mol Plant. 2017 Nov 6;10(11):1387-1399
pubmed: 28965832
Biochemistry. 1999 Dec 7;38(49):16105-14
pubmed: 10587433
Genome Biol. 2017 Jan 5;18(1):1
pubmed: 28077169
Nat Biotechnol. 2019 Apr;37(4):424-429
pubmed: 30804537
Angew Chem Int Ed Engl. 2023 Jun 26;62(26):e202304756
pubmed: 37118885
Phys Rev B Condens Matter. 1988 Jan 15;37(2):785-789
pubmed: 9944570
Genes (Basel). 2019 Jan 30;10(2):
pubmed: 30704115
Proc Natl Acad Sci U S A. 1992 Mar 1;89(5):1827-31
pubmed: 1542678
Methods Enzymol. 2015;560:297-329
pubmed: 26253976
Acc Chem Res. 2000 Apr;33(4):253-60
pubmed: 10775318
PLoS Genet. 2013 Jun;9(6):e1003602
pubmed: 23825970
J Phys Chem B. 2007 May 17;111(19):5386-95
pubmed: 17447808
Nucleic Acids Res. 2009 Feb;37(2):e12
pubmed: 19059995
Nucleic Acids Res. 2010 Mar;38(5):1415-30
pubmed: 20007150
Chembiochem. 2016 Jun 16;17(12):1102-6
pubmed: 26972311
Angew Chem Int Ed Engl. 2018 Apr 9;57(16):4296-4312
pubmed: 28941008
Nat Cell Biol. 2019 May;21(5):552-559
pubmed: 31048770
Proc Natl Acad Sci U S A. 2019 Apr 2;116(14):6784-6789
pubmed: 30872485
Curr Chem Genomics. 2012;6:55-71
pubmed: 23248739
Chem Rev. 2016 Sep 14;116(17):10075-166
pubmed: 27285582
J Am Chem Soc. 2007 Jun 27;129(25):8034-40
pubmed: 17547405
Int J Mol Sci. 2022 Nov 10;23(22):
pubmed: 36430347
Chembiochem. 2021 Dec 2;22(23):3333-3340
pubmed: 34498783
Nucleic Acids Res. 1980 Oct 24;8(20):4777-90
pubmed: 7443525