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1.
Angew Chem Int Ed Engl ; 53(1): 315-8, 2014 Jan 03.
Artigo em Inglês | MEDLINE | ID: mdl-24281791

RESUMO

A 5-formyl-2'-deoxycytidine (fdC) phosphoramidite building block that enables the synthesis of fdC-containing DNA with excellent purity and yield has been developed. In combination with phosphoramidites for 5-methyl-dC, 5-hydroxymethyl-dC, and carboxy-dC, it was possible to prepare a segment of the OCT-4 promoter that contains all four epigenetic bases. Because of the enormous interest in these new epigenetic bases, the ability to insert all four of them into DNA should be of great value for the scientific community.


Assuntos
DNA/síntese química , Desoxicitidina/análogos & derivados , Nucleosídeos/genética , Desoxicitidina/síntese química , Epigênese Genética , Estrutura Molecular
2.
Chemistry ; 17(49): 13782-8, 2011 Dec 02.
Artigo em Inglês | MEDLINE | ID: mdl-22069110

RESUMO

5-Formylcytosine (fC or (5-CHO)dC) and 5-carboxylcytosine (caC or (5-COOH)dC) have recently been identified as constituents of mammalian DNA. The nucleosides are formed from 5-methylcytosine (mC or (5-Me)dC) via 5-hydroxymethylcytosine (hmC or (5-HOMe)dC) and are possible intermediates of an active DNA demethylation process. Here we show efficient syntheses of phosphoramidites which enable the synthesis of DNA strands containing these cytosine modifications based on Pd(0)-catalyzed functionalization of 5-iododeoxycytidine. The first crystal structure of fC reveals the existence of an intramolecular H-bond between the exocyclic amine and the formyl group, which controls the conformation of the formyl substituent. Using a newly designed in vitro mutagenicity assay we show that fC and caC are only marginally mutagenic, which is a prerequisite for the bases to function as epigenetic control units.


Assuntos
Citosina/análogos & derivados , Citosina/síntese química , Mutagênicos/síntese química , Mutagênicos/farmacologia , Oligonucleotídeos/síntese química , Oligonucleotídeos/farmacologia , 5-Metilcitosina/análogos & derivados , Cromatografia Líquida de Alta Pressão , Citosina/química , Citosina/farmacologia , Metilação de DNA , Estrutura Molecular , Mutagênicos/química , Oligonucleotídeos/química , Compostos Organofosforados/química , Espectrometria de Massas por Ionização por Electrospray
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