Deoxycytidine , structure

In a similar biochemically oriented vein, several papers were published during 2003 in the journal Chemical Research in Toxicology, representing yet another area of applicability of 3 mm NMR probe capabilities. In the first of these reports, Hankin et al.159 described the results of an investigation into the covalent binding of leukotriene A4 to DNA and RNA. Later in 2003, Blair and co-workers160 reported on the characterization of 2 -deoxycytidine adducts derived from 4-oxo-2-nonenal, a novel lipid peroxidation product. Two of the adducts characterized, Ai and A2, were consistent with substituted ethano-deoxycytidine structures. The third adduct, B, was characterized as a 7-heptanone-etheno-deoxycytidine adduct (78). 

Write a structural formula for 2 -deoxycytidine 3 -monophos- phate. You may wish to refer to Table 28.2 for the structure of cytidine. J... 

The 2 -chloro and 2 -bromo congeners of either 748 (FIAC) or 758 (FMAU) are more cytotoxic than FIAC and FMAU, suggesting that these chloro and bromo nucleosides, in contrast to the 2 -fluoro compounds, are comparatively better substrates for deoxycytidine kinase of human lymphocytes than the substrates for viral-specific thymidine kinase. The disposition of the 2 -fluoro group may also be important from the biological viewpoint. It should be noted that the structural difference between RNA and DNA is at the 2 -position. The ribo type of analog (738) of FIAC is 10 times less effective in suppression of HSV replication than is FIAC. Thus Fox, and Watanabe and coworkers concluded that the 2 - up fluorine disposition and the species of the substituent at C-5 are the two important factors influencing antiviral activity. Nevertheless, the mechanism of action of 2 -deoxy-2 -fluorocytidine (737) on certain herpes viruses, including HSV-1... 

Figure 5.10 Single-crystal x-ray structure of 2 -deoxycytidine-N(3)-cyanoborane with a BH- HN(4) distance of 2.05 A. (Reproduced with permission from ref. 14.)...

Draw the complete structure of deoxycytidine 5 -phosphate, one of the four deoxyribonucleotides. 

Another experimental verification of theoretical data may be provided by the analysis of a range of variation of endocyclic torsion angles in crystal structures containing uracil and cytosine fragments. It was demonstrated [32] that range of variation of the N1-C2-N3-C4 torsion angle in uracil and the C6-N1-C2-N3 torsion angle in cytosine amounts to 12-13°. For example, it was found that the value of the C6-N1-C2-N3 in the crystal of 5-bromo-2 -deoxycytidine is —7.1°, —12.4°, and — 13.9°, respectively, for three molecules in asymmetrical part of unit cell [39],... 

Fig. 21.5 Structure of orthogonal conformers of 2 -deoxyriboadenosine monophosphate (AMP) and 2 -deoxycytidine monophosphate (CMP) with nonplanar pyrimidine ring according to calculations at the B3LYP/aug-cc-pvdz level [4]...

Figure 4 Molecular structures of five DNA nucleosides 2 -deoxyuridine (dU), 2 -de-oxythymidine (dT), 2 -deoxycytidine (dC), 2 -deoxyguanosine (dG), and 2 -deoxyadeno-sine (dA).

Gemcitabine [gem SITE ah bean] is an analog of the nucleoside deoxycytidine its chemical structure is 2 2 -difluorodeoxycytidine (dFdC). Its use is indicated in the first-line treatment of locally advanced or metastatic adenocarcinoma of the pancreas. It has also shown some activity against other tumors. 

With two independent molecules A and B in the asymmetric unit (Fig. 17.34), the hydrogen-bond structure of 2 -deoxycytidine [DXCYTD] contains an interesting, almost symmetrical, cyclic tetramer, to which is attached a finite chain of three hydroxyl groups. 

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