An Efficient Synthesis of Pyrimidine Specific 2′-Deoxynucleoside-5′-Tetraphosphates

An efficient chemical synthesis of pyrimidine specific 2′-deoxynucleoside-5′-tetraphosphates, such as 2′-deoxycytidine-5′-tetraphosphate (dC4P) and thymidine-5′-tetraphosphate (T4P) is described. The present three-step synthetic strategy involves monophosphorylation of 2′-deoxynucleoside using phosp...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2012-07, Vol.31 (7), p.567-573
Main Authors: Kore, Anilkumar R., Xiao, Zejun, Senthilvelan, Annamalai, Charles, Irudaya, Shanmugasundaram, Muthian, Mukundarajan, Sriram, Srinivasan, Balasubramanian
Format: Article
Language:English
Subjects:
2′-Deoxynucleoside-5′-tetraphosphates
Chemistry Techniques, Synthetic - economics
Chemistry Techniques, Synthetic - methods
Deoxyribonucleosides - chemical synthesis
Deoxyribonucleosides - chemistry
DNA sequencing
Imidazoles - chemical synthesis
Imidazoles - chemistry
imidazolide salt
Phosphorylation
Polyphosphates - chemical synthesis
Polyphosphates - chemistry
Pyrimidines - chemical synthesis
Pyrimidines - chemistry
zinc chloride
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Summary:An efficient chemical synthesis of pyrimidine specific 2′-deoxynucleoside-5′-tetraphosphates, such as 2′-deoxycytidine-5′-tetraphosphate (dC4P) and thymidine-5′-tetraphosphate (T4P) is described. The present three-step synthetic strategy involves monophosphorylation of 2′-deoxynucleoside using phosphorous oxychloride, conversion of 5′-monophosphate into the corresponding imidazolide salt, followed by reaction with tris[tributylammonium] triphosphate leading to the 2′-deoxynucleoside-5′-tetraphosphate in good yields.
ISSN:1525-7770
1532-2335
DOI:10.1080/15257770.2012.703358