Literature DB >> 21648398

Syntheses of 5-formyl- and 5-carboxyl-dC containing DNA oligos as potential oxidation products of 5-hydroxymethylcytosine in DNA.

Qing Dai1, Chuan He.   

Abstract

To investigate the potential oxidation products of 5-hydroxymethylcytosine (5-hmC)-containing DNA, we present here efficient syntheses of 5-formyl- and 5-methoxycarbonyl-2'-deoxycytidine phosphoramidites. The 5-formyl group in III was easy to introduce and was compatible with phosphoramidite and DNA syntheses. An additional treatment of ODN1 with NaBH(4) produced the corresponding ODN2 quantitatively. Phosphoramidite V was also incorporated into DNA, and the methyl ester could be hydrolyzed under mild basic conditions to afford ODN3.

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Year:  2011        PMID： 21648398      PMCID： PMC3150843          DOI： 10.1021/ol201189n

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  15 in total

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3.  Synthesis and properties of oligonucleotides containing 5-formyl-2'-deoxycytidine: in vitro DNA polymerase reactions on DNA templates containing 5-formyl-2'-deoxycytidine.

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Review 4.  Active DNA demethylation: many roads lead to Rome.

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5.  A proficient enzyme.

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6.  Syntheses of two 5-hydroxymethyl-2'-deoxycytidine phosphoramidites with TBDMS as the 5-hydroxymethyl protecting group and their incorporation into DNA.

Authors:  Qing Dai; Chun-Xiao Song; Tao Pan; Chuan He
Journal:  J Org Chem       Date:  2011-04-14       Impact factor: 4.354

7.  Conversion of 5-methylcytosine to 5-hydroxymethylcytosine in mammalian DNA by MLL partner TET1.

Authors:  Mamta Tahiliani; Kian Peng Koh; Yinghua Shen; William A Pastor; Hozefa Bandukwala; Yevgeny Brudno; Suneet Agarwal; Lakshminarayan M Iyer; David R Liu; L Aravind; Anjana Rao
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  17 in total

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Journal:  Cell       Date:  2013-04-18       Impact factor: 41.582

5.  Weakened N3 Hydrogen Bonding by 5-Formylcytosine and 5-Carboxylcytosine Reduces Their Base-Pairing Stability.

Authors:  Qing Dai; Paul J Sanstead; Chunte Sam Peng; Dali Han; Chuan He; Andrei Tokmakoff
Journal:  ACS Chem Biol       Date:  2015-12-17       Impact factor: 5.100

6.  A Chemical Probe Targets DNA 5-Formylcytosine Sites and Inhibits TDG Excision, Polymerases Bypass, and Gene Expression.

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7.  Fragmentation of electrospray-produced deprotonated ions of oligodeoxyribonucleotides containing an alkylated or oxidized thymidine.

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9.  Enzymatic analysis of Tet proteins: key enzymes in the metabolism of DNA methylation.

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10.  Tet proteins can convert 5-methylcytosine to 5-formylcytosine and 5-carboxylcytosine.

Authors:  Shinsuke Ito; Li Shen; Qing Dai; Susan C Wu; Leonard B Collins; James A Swenberg; Chuan He; Yi Zhang
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