1361013-59-3

Upstream product

• 1257247-38-3 5-formyl-3′,5′-bis-(tert-butyl-dimethylsilyl)-2′-deoxy-cytidine 
• 1361013-57-1 3',5'-(tert-butyldimethylsilyl)-4-N-benzoyl-5-formyl-2'deoxycytidine 
• 838-07-3 5-methyldeoxycytidine 
• 137017-45-9 5-formyl-2′-deoxycytidine 
• 93-97-0 benzoic acid anhydride 
• 478843-96-8 5-iodo-3'O,5'O-bis(tert-butyldimethylsilyl)-2'-deoxycytidine 

Downstream Products

• 1361013-62-8 5'-(4,4'-dimethoxytrityl)-4-N-benzoyl-5-formyl-2'-deoxycytidine 
• 1361013-60-6 3'-(diisopropylamino-cyanoethoxyphosphino)-5'-(4,4'-dimethoxytrityl)-4-N-benzoyl-5-formyl-2'deoxycytidine 

Relevant academic research and scientific papers

5-Hydroxymethylcytosine and 5-formylcytosine containing deoxyoligonucleotides: Facile syntheses and melting temperature studies

An oxidation-based synthetic approach was developed for facile preparation of 5-formyl-2′-deoxycytidine and 5-hydroxymethyl-2′-deoxycytidine phosphoramidites. Upon introducing organic solvent components and copper catalysts, C5-methyl groups of 5-methyl-2′-deoxycytidine and thymidine were readily oxidized to formyl and hydroxyl functionality, respectively. Standard solid phase DNA synthesis and conventional deprotection methods were applicable to synthesize 5-formyl- or 5-hydroxymethyl-cytosine containing DNA oligonucleotides, which were used to study the effect of epigenetic modifications on DNA thermal dynamic stability.

Improved synthesis and mutagenicity of oligonucleotides containing 5-hydroxymethylcytosine, 5-formylcytosine and 5-carboxylcytosine

5-Formylcytosine (fC or 5-CHOdC) and 5-carboxylcytosine (caC or 5-COOHdC) have recently been identified as constituents of mammalian DNA. The nucleosides are formed from 5-methylcytosine (mC or 5-MedC) via 5-hydroxymethylcytosine (hmC or 5-HOMedC) 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 Pd0-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.