High Fidelity Enzyme-Free Primer Extension with an Ethynylpyridone Thymidine Analog.
C-nucleosides
antivirals
genetic copying
nucleotides
replication
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
17 Nov 2021
17 Nov 2021
Historique:
received:
16
08
2021
pubmed:
25
9
2021
medline:
19
11
2021
entrez:
24
9
2021
Statut:
ppublish
Résumé
High fidelity base pairing is important for the transmission of genetic information. Weak base pairs can lower fidelity, complicating sequencing, amplification and replication of DNA. Thymidine 5'-monophosphate (TMP) is the most weakly pairing nucleotide among the canonical deoxynucleotides, causing high errors rates in enzyme-free primer extension. Here we report the synthesis of an ethynylpyridone C-nucleoside analog of 3'-amino-2',3'-dideoxythymidine monophosphate and its incorporation in a growing strand by enzyme-free primer extension. The ethynylpyridone C-nucleotide accelerates extension more than five-fold, reduces misincorporation and readily displaces TMP in competition experiments. The results bode well for the use of the C-nucleoside as replacements for thymidine in practical applications.
Identifiants
pubmed: 34559417
doi: 10.1002/chem.202102996
pmc: PMC9293356
doi:
Substances chimiques
DNA Primers
0
Nucleotides
0
DNA
9007-49-2
Thymidine
VC2W18DGKR
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
15918-15921Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : project-ID 364653263 - TRR 235
Organisme : Volkswagen Foundation
ID : Az 92 768
Informations de copyright
© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
Angew Chem Int Ed Engl. 2017 Sep 4;56(37):11037-11043
pubmed: 28514493
Chem Rev. 2009 Dec;109(12):6729-64
pubmed: 19761208
Chem Commun (Camb). 2005 Oct 21;(39):4922-4
pubmed: 16205800
Angew Chem Int Ed Engl. 2018 Jan 8;57(2):417-421
pubmed: 29115744
Chemistry. 2021 Nov 17;27(64):15918-15921
pubmed: 34559417
Chem Biodivers. 2021 Jan;18(1):e2000937
pubmed: 33270983
Biochem Soc Trans. 2009 Apr;37(Pt 2):454-9
pubmed: 19290881
Comput Struct Biotechnol J. 2021 Feb 23;19:1312-1324
pubmed: 33738080
Angew Chem Int Ed Engl. 2012 Aug 13;51(33):8299-303
pubmed: 22777755
Beilstein J Org Chem. 2018 Mar 12;14:603-617
pubmed: 29623122
Angew Chem Int Ed Engl. 2018 Jul 16;57(29):8911-8915
pubmed: 29779237
Antiviral Res. 2019 Feb;162:5-21
pubmed: 30529089
Mol Biol (Mosk). 2000 Nov-Dec;34(6):921-30
pubmed: 11153470
J Am Chem Soc. 2013 Jan 9;135(1):354-66
pubmed: 23259600
J Mol Evol. 1977 Aug 5;9(4):323-8
pubmed: 302339
J Am Chem Soc. 2006 Jan 18;128(2):396-7
pubmed: 16402811
Angew Chem Int Ed Engl. 2018 Aug 20;57(34):11074-11077
pubmed: 29766621
Nucleic Acids Res. 2016 Jul 8;44(12):5504-14
pubmed: 27235418
Angew Chem Int Ed Engl. 2005 Oct 21;44(41):6746-50
pubmed: 16187384
Angew Chem Int Ed Engl. 2005 Oct 14;44(40):6588-92
pubmed: 16175646
Angew Chem Int Ed Engl. 2006 Sep 18;45(37):6144-8
pubmed: 16927357
Chem Commun (Camb). 2016 Mar 4;52(18):3684-6
pubmed: 26857159
Radiol Technol. 2013 Jan-Feb;84(3):247-67; quiz p.268-70
pubmed: 23322863
J Am Chem Soc. 2015 Feb 25;137(7):2769-75
pubmed: 25654265
Nature. 2003 Jan 23;421(6921):431-5
pubmed: 12540917
Chem Rev. 2014 Jan 8;114(1):285-366
pubmed: 24171674
Antiviral Res. 2018 Jun;154:66-86
pubmed: 29649496
Org Lett. 2007 May 24;9(11):2223-5
pubmed: 17480087
Nucleic Acids Res. 2014 Jun;42(11):7409-20
pubmed: 24875480
Chem Biodivers. 2007 Apr;4(4):784-802
pubmed: 17443889
J Am Chem Soc. 2014 Oct 1;136(39):13916-24
pubmed: 25188906
Nucleosides Nucleotides Nucleic Acids. 2013;32(1):17-27
pubmed: 23360292
Antimicrob Agents Chemother. 2021 Jun 17;65(7):e0082021
pubmed: 34137638
Nucleosides Nucleotides Nucleic Acids. 2006;25(12):1309-33
pubmed: 17067955
Angew Chem Int Ed Engl. 2013 Oct 4;52(41):10874-7
pubmed: 24038815
Proc Natl Acad Sci U S A. 2010 Jul 6;107(27):12074-9
pubmed: 20554916
Protein Sci. 2019 Jun;28(6):990-1004
pubmed: 30945375
Nat Chem. 2011 Jul 10;3(8):603-8
pubmed: 21778979
J Phys Chem B. 2014 Jun 19;118(24):6586-96
pubmed: 24857638
Nucleic Acids Res. 2018 Sep 19;46(16):8069-8078
pubmed: 30085103
Proc Natl Acad Sci U S A. 2013 Oct 29;110(44):17732-7
pubmed: 24101473