Deoxyuridine 5 -phosphate

P—S bond is elongated to 196.5 pm and the P—0(H) bond shortened to 148 pm.164 The structures of the m-vinyl carbonate (136)165 and the cyclic phosphonic anhydride (96)123 have been determined, and for the latter compound the ring was found to be almost planar. A -Ray diffraction data of deoxyuridine phosphate,166 phospholipid multilayers,167 nucleotides,168 and skeletal muscle169 have been analysed. The crystal structure of the phosphazene (137) has been established.170... 

Metabolism of the pyrimidine deoxyribonucleotides is more complex because, in addition to transfer of phosphoryl groups, deamination and methylation reactions occur at this level. Specifically, the thymidine phosphates are derived by methylation of deoxyuridylate, and the latter may be derived from the deoxycytidine phosphates by way of deoxycytidylate deaminase. The deoxycytidine phosphates are not formed by amination of deoxyuridine phosphates, but are derived entirely from the cytidine phosphates by enzymatic reduction (Chapter 16). 

CQHuNjNajOgP S H20 2 -Deoxyuridine 5 -(disodium phosphate), pentahydrate (NADOUR)186... 

Ci9H24N70,2P-4 H20 Adenosine 5 -(2 -deoxyuridin-2 -yl phosphate), tetrahydrate ADURPOIO 31 371... 

On the other hand, the presence of a glycosyl group attached to the nucleoside pyrophosphate has been found to influence the reactivity of the heterocyclic base. Thus, the catalytic hydrogenation of uridine and 6-azauridine 5 -(a-D-glucopyranosyl pyrophosphates) to the 5,6-dihydro derivatives proceeds more slowly than that of the respective nucleoside 5 -phosphates or 5 -pyrophosphates.338,339 Such differences have not been observed in comparisons of analogous derivatives of 2 -deoxyuridine, N3-methyluridine, and cytidine. 

Uridine 5 -phosphate or 5 -pyrophosphate and 2 -deoxyuridine 5 -phosphate react with hydroxylamine approximately 1.5 times faster than the related 5 -(a-D-glucopyranosyl pyrophosphates), whereas the velocities are the same for reactions of the corresponding... 

Hildenbrand K (1990) The S04-induced oxidation of 2 -deoxyuridine-5 -phosphate, uridine-5 -phosphate and thymidine-5 -phosphate. An ESR study in aqueous solution. Z Naturforsch 45c 47-58... 

Photochemical reaction in acetonitrile of 2 -deoxyuridine 5 -phosphate with the halo-heteroarenes 2-iodothiophene, 2-iodofuran, l-methyl-2-iodopyrrole and 3-iodothiophene affords the C-5 heteroaryl substituted nucleotides518.6-Aryluridines have been prepared by irradiation of 6-iodouridines in benzene, anisole, thiophene, Af-methylpyrrole or 2-methyl-furan in the presence of triethylamine519. 

Kornberg s work on the biosynthesis of deoxyribonucleic acid has shown that enzymes in Escherichia coli extracts catalyze the formation of the 5-triphosphates of 2-deoxyadenosine, 2-deoxyguanosine, 2-deoxycyti-dine, and thymidine from the corresponding monophosphates in the presence of adenosine 5-triphosphate, but fail to catalyze phosphorylation of deoxyuridine 5-phosphate this finding could explain why uracil is not a constituent of deoxyribonucleic acid. 

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