1277097-09-2Relevant articles and documents
An efficient PyAOP-based C4-amination method for direct access of oxidized 5MedC derivatives
Zheng, Xiu-An,Huang, Hua-Shan,Kong, Rui,Chen, Wei-Jie,Gong, Shan-Shan,Sun, Qi
, p. 7095 - 7101 (2018)
In the past decade, synthetic oxidized 5-MedC nucleosides and their derivatives have become essential tools for epigenetic research. The low efficacy of both conventional and newly reported BOP methods on C4-amination of these specific oxidized 5-MedU substrates urged us to systematically investigate how the nature of onium salt-based coupling reagents affects the C4-amination of pyrimidine nucleobases and lead us to the findings that different onium coupling reagents result in the formation of distinctive activation intermediates and PyAOP is much more potent than BOP in both activation and aminolysis steps. Direct amination without the need of ribose protection, ultrafast activation, tolerance to aqueous N-nucleophiles, and excellent yields for diverse oxidized 5MedC derivatives are the advantages of this PyAOP-based C4-amination method.
5-Hydroxymethylcytosine and 5-formylcytosine containing deoxyoligonucleotides: Facile syntheses and melting temperature studies
Xuan, Shuguang,Wu, Qiong,Cui, Liang,Zhang, Dawei,Shao, Fangwei
supporting information, p. 1186 - 1191 (2015/03/14)
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 of 5-hydroxymethyl-2′-deoxycytidine phosphoramidite using a 2′-deoxyuridine to 2′-deoxycytidine conversion without temporary protecting groups
Hansen, Anders S.,Thalhammer, Armin,El-Sagheer, Afaf H.,Brown, Tom,Schofield, Christopher J.
, p. 1181 - 1184 (2011/04/16)
5-Hydroxymethylcytosine has recently been characterized as the 'sixth base' in human DNA. To enable research on this DNA modification, we report an improved method for the synthesis of 5-hydroxymethyl-2′-deoxycytidine (5-HOMedC) phosphoramidite for site-specific incorporation into oligonucleotides. To minimize manipulations we employed a temporary protecting group-free 2′-deoxyuridine to 2′-deoxycytidine conversion procedure that utilizes phase transfer catalysis. The desired 5-HOMedC phosphoramidite is obtained in six steps and 24% overall yield from 2′-deoxyuridine.
Hydroxylation of methylated CpG dinucleotides reverses stabilisation of DNA duplexes by cytosine 5-methylation
Thalhammer, Armin,Hansen, Anders S.,El-Sagheer, Afaf H.,Brown, Tom,Schofield, Christopher J.
, p. 5325 - 5327 (2011/06/21)
Cytosine-5-methylation stabilises DNA duplexes and is associated with transcriptional repression; 5-methylcytosine undergoes hydroxylation to 5-hydroxymethylcytosine, a modification of unknown biological function. Spectroscopic and calorimetric analyses show that 5-hydroxymethylcytosine introduction reverses the stabilising effect of 5-methylcytosine, suggesting that in some contexts, 5-methylcytosine hydroxylation may, along with other factors, contribute to the alleviation of transcriptional repression.
