Simple alkanoyl acylating agents for reversible RNA functionalization and control.
Journal
Chemical communications (Cambridge, England)
ISSN: 1364-548X
Titre abrégé: Chem Commun (Camb)
Pays: England
ID NLM: 9610838
Informations de publication
Date de publication:
25 Apr 2019
25 Apr 2019
Historique:
pubmed:
13
4
2019
medline:
5
6
2019
entrez:
13
4
2019
Statut:
ppublish
Résumé
We describe the synthesis and RNA acylation activity of a series of minimalist azidoalkanoyl imidazole reagents, with the aim of functionalizing RNA at 2'-hydroxyl groups at stoichiometric to superstoichiometric levels. We find marked effects of small structural changes on their ability to acylate and be reductively removed, and identify reagents and methods that enable efficient RNA functionalization and control.
Identifiants
pubmed: 30977472
doi: 10.1039/c9cc01598a
pmc: PMC6541391
mid: NIHMS1025682
doi:
Substances chimiques
Aptamers, Nucleotide
0
Azides
0
Imidazoles
0
Indicators and Reagents
0
Phosphines
0
RNA
63231-63-0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
5135-5138Subventions
Organisme : NIGMS NIH HHS
ID : R01 GM127295
Pays : United States
Références
Annu Rev Biomed Eng. 2009;11:25-47
pubmed: 19400712
J Am Chem Soc. 2005 Dec 14;127(49):17286-95
pubmed: 16332078
Wiley Interdiscip Rev RNA. 2014 Nov-Dec;5(6):867-81
pubmed: 25132067
Methods. 2011 Jun;54(2):251-9
pubmed: 21354310
J Am Chem Soc. 2006 Apr 12;128(14):4598-611
pubmed: 16594697
Nat Genet. 2001 Aug;28(4):317-25
pubmed: 11479592
Nat Chem Biol. 2013 Jan;9(1):18-20
pubmed: 23178934
Biochem Biophys Res Commun. 2006 Jun 9;344(3):887-92
pubmed: 16631608
RNA. 2007 Aug;13(8):1384-9
pubmed: 17548432
J Am Chem Soc. 2005 Mar 30;127(12):4223-31
pubmed: 15783204
Angew Chem Int Ed Engl. 2016 Aug 22;55(35):10283-6
pubmed: 27431506
Nat Struct Mol Biol. 2014 Aug;21(8):658-63
pubmed: 25026079
Curr Opin Chem Biol. 2009 Dec;13(5-6):678-86
pubmed: 19857985
Chem Commun (Camb). 2016 Jun 7;52(45):7284-7
pubmed: 27181840
ACS Chem Biol. 2016 May 20;11(5):1347-53
pubmed: 26942998
Nat Biotechnol. 1996 Mar;14(3):303-8
pubmed: 9630890
Nat Chem Biol. 2018 Mar;14(3):276-283
pubmed: 29334380
Nucleic Acids Res. 2012 Aug;40(14):6765-73
pubmed: 22564896
Angew Chem Int Ed Engl. 2016 Aug 26;55(36):10899-903
pubmed: 27511141
J Inorg Biochem. 2015 Sep;150:182-8
pubmed: 25865001
Anal Bioanal Chem. 2008 Feb;390(4):1009-21
pubmed: 17891385
J Am Chem Soc. 2007 Apr 11;129(14):4144-5
pubmed: 17367143
Mol Biosyst. 2008 May;4(5):431-40
pubmed: 18414741
Bioorg Med Chem Lett. 2018 Feb 15;28(4):601-605
pubmed: 29398542
Nature. 2015 Mar 26;519(7544):486-90
pubmed: 25799993
Angew Chem Int Ed Engl. 2013 Jul 22;52(30):7874-8
pubmed: 23794451
Structure. 2010 Jul 14;18(7):787-97
pubmed: 20637415
Biophys J. 2018 Feb 6;114(3):688-700
pubmed: 29414714
PLoS One. 2013 Nov 14;8(11):e79142
pubmed: 24244437
Science. 2011 Jul 29;333(6042):642-6
pubmed: 21798953
Nucleic Acids Res. 1978 Oct;5(10):3665-77
pubmed: 724498
Chembiochem. 2010 Mar 1;11(4):469-80
pubmed: 20135663
J Am Chem Soc. 2018 Mar 14;140(10):3491-3495
pubmed: 29474085
Chem Commun (Camb). 2012 Nov 14;48(88):10835-7
pubmed: 23032097
Methods. 2016 Apr 1;98:18-25
pubmed: 26615954
J Am Chem Soc. 2011 Dec 14;133(49):19878-88
pubmed: 21981600
Angew Chem Int Ed Engl. 2018 Mar 12;57(12):3059-3063
pubmed: 29370460
Nucleic Acids Res. 1996 Nov 15;24(22):4535-42
pubmed: 8948646
J Chromatogr A. 2014 Aug 15;1355:1-14
pubmed: 24951289