Uridine selective phosphorylation

Nucleoside Acyclic Phosphates. - 2.1.1 Mononucleoside Phosphate Derivatives. A preliminary study on a novel solid phase reagent (Scheme 1) for the capture phosphorylation of nucleosides has been described. The 1 % cross-linked divinylbenzene-polystyrene copolymer, containing cyanoethoxy iV,AT-diisop-ropyl phosphine was used for the selective phosphorylation of uridine to 5 -uridine monophosphate (UMP) in 67% yield. ... 

Phosphonate esters can be readily prepared from alcohols and phosphonic acid derivatives. The selective phosphorylation of the 5 -hydroxy groups of thymidine and uridine was originally reported Mitsunobu s group in 1969. More recent examples include the modified derivative of the antitumor C-nucleoside tiazofurin (240) and an AZT triphosphate analog (241) shown... 

THYMIDINE KINASE (TK) An enzyme involved in the utilization of the nucleoside thymidine (which ultimately becomes part of the structure of DNA) catalyzes the phosphorylation of thymidine to thymidine monophosphate mutants that lack TK are resistant to the toxic effects of several thymidine analogues, including bromodeoxy-uridine and trifluorothymidine selection of these drug-resistant mutants provides the basis of several... 

Iododeoxyuridine is a derivative of uridine used to combat herpesvirus. The viral enzyme, deoxypyrimidine kinase, readily phosphorylates 5-iododeoxyuridine and the viral DNA polymerase attempts, in turn, to incorporate them into DNA in place of the corresponding dNTP.The drug interferes with DNA replication. Uninfected cells phosphorylate 5-iododeoxyuridine only weakly, so DNA replication and virus growth are inhibited selectively in infected cells. 

Other nucleoside 5 -triphosphates demonstrate a standard free energy of hydrolysis equivalent to that of ATP. Their intracellular concentrations are low which restricts their function to selected biosynthetic pathways, e.g. uridine triphosphate (UTP) in glycogen biosynthesis (Section 11.5). Nucleoside-diphosphate kinase permits the phosphorylation of (d)NDPs to (d)NTPs at the expense of ATP and vice versa. 

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