5-formyl-2 -deoxyuridine

The HPLC-MS/MS method has been recently applied for the measurement of the cis and trans diastereomers of 5,6-dihydroxy-5,6-dihydrothymidine (8), 5-formyl-2 -deoxyuridine (11) and 5-(hydroxymethyl)-2 -deoxyuridine (10) within cellular DNA exposed to ionizing radiation and heavy particles. The two methyl oxidation products 10 and 11 and thymidine glycols 8 (Chart 3) that are produced within the range of 20 to 100 lesions per 10 normal bases and per Gy (Table 3) are likely to be derived from the decomposition of 5-(hydroperoxymethyl)-2 -deoxyuridine (7) and 5-(6)-hydroperoxy-6-(5)-hydroxy-5,6-dihydrothymidine 5 and 6, respectively. 

Formamido lesion within ODNs and DNA 5-Formyl-2 -deoxyuridine 5-Formyl-2 -deoxyuridine 5-Formyl-2 -deoxyuridine in DNA 5-Formyluracil... 

A new method for the synthesis oligonucleotides containing of 5-formyl-2 -deoxyuridine has been described. The protected phosphoramidite of 5-(l,2-dihydroxyethyl)-2 -deoxyuridine (181) was prepared from 5-iodo-2 -deoxyuridine in seven steps. Following deprotection of the oligomer, subsequent oxidation of the diol with sodium periodate yielded the formyl function which could also be reduced with sodium borohydride to yield the 5-hydroxymethyl compound. An... 

Methotrexate (MTX, chemical structure shown in Fig. 1.) competitively inhibits the dehyrofolate reductase, an enzyme that plays an essential role in purine synthesis. The dehydrofolate reductase regenerates reduced folates when thymidine monophosphate is formed from deoxyuridine monophosphate. Without reduced folates cells are unable to synthesize thymine. Administration of N-5 tetrahydrofolate or N-5 formyl-tetrahydrofolate (folinic acid) can bypass this block and rescue cells from methotrexate activity by serving as antidote. 

AflBnity Labellii. —Of a large number of 5-substituted-2 -deoxyuridine 5 -mono-phosphates prepared as potential inhibitors of thymidylate kinase, 5-formyl-dUMP was found to be a potent non-competitive inhibitor of the enzyme from calf thymus, and 5-azidomethyl-dUMP irreversibly inactivated both this enzyme and the enzyme from Ehrlich ascites tumour cells. Protection by cofactor addition could only be demonstrated for the latter case, however. 5-Iodoacetamidomethyl-dUMP (68) irreversibly inactivates the tumour enzyme more rapidly than the calf thymus enzyme, and protection could also be demonstrated in this case it has therefore been claimed that (68) is isozyme-specific for the tumour enzyme. ... 

One-carbon pool Folate derivatives that carry a single carbon in various oxidation states (formyl, methenyl, methylene, and methyl) for transfer to acceptor molecules that is, transfer to deoxyuridine monophosphate to form deoxythymidine monophosphate transfer to homocysteine to form methionine. 

A number of 5-(2-subsituted-vinyl)-6-aza-2 -deoxyuridines have been prepared conventionally from the appropriately substituted uracil base, or more satisfactorily by modifying preformed 5-hydroxymethyl-6-aza-2 -deoxyuridine via the corresponding 5-formyl compound a 5-(3-furanyl) analogue was best made by 2 -deoxygenation of the ribose analogue, via a 3, 5 -tetraisopropyldisiloxanyl intermediate. 

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