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Chemical Compound Review

dCMP     [(2R,3S,5R)-5-(4-amino-2-oxo- pyrimidin-1...

Synonyms: SureCN48317, CHEMBL374699, AG-D-13826, CHEBI:15918, D7750_SIGMA, ...
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Disease relevance of deoxycytidylic acid

  • Crystal structure of deoxycytidylate hydroxymethylase from bacteriophage T4, a component of the deoxyribonucleoside triphosphate-synthesizing complex [1].
  • We have cloned cDNA copies of human preproparathyroid hormone in Escherichia coli after insertion of double-stranded DNA into the Pst I site of plasmid pBR322 using the poly(dG) . poly(dC) homopolymer extension technique [2].
  • The enzyme was purified to homogeneity and found to possess properties similar to T2 phage deoxycytidylate deaminase [3].
  • Gel electrophoresis was used to analyze the effect of inhibitors on extension of heteropolymeric template-primers by HIV-1 reverse transcriptase. ddCTP induced accumulation of partially extended primers which had been terminated at sites requiring incorporation of deoxycytidylate [4].
  • Deoxycytidylate deaminase from Bacillus subtilis. Purification, characterization, and physiological function [5].

High impact information on deoxycytidylic acid


Chemical compound and disease context of deoxycytidylic acid

  • The activity of deoxycytidylate aminohydrolase, a pivotal enzyme for pyrimidine biosynthesis in mammalian tissue, is 100x greater in the Novikoff hepatoma harvested from the intraperitoneal cavity than in the same tumor excised from either subcutaneous or intramuscular sites [10].
  • In order to study the influence of 3-methylcytosine on DNA replication, untreated and DMS-treated poly(dC) were used as templates for E. coli DNA polymerase I. The alkylation of poly(dC) inhibits DNA chain elongation, and does not induce any mispairing under high fidelity conditions [11].

Biological context of deoxycytidylic acid


Anatomical context of deoxycytidylic acid


Associations of deoxycytidylic acid with other chemical compounds


Gene context of deoxycytidylic acid

  • The cd gene of bacteriophage T4, which encodes the enzyme deoxycytidylate deaminase, was isolated as a 1.9-kilobase DNA fragment and completely sequenced [3].
  • A genetic ('transformation') assay was used to monitor transcription of genes 30 (polynucleotide ligase), 42 (deoxycytidylate hydroxymethylase), 43 (DNA polymerase), rIIA, rIIB, and e (endolysin) [26].
  • In contrast, cotransfection of the tk gene with polymers which do not assume Z-conformation such as, poly(dG) X poly(dC) or poly(dA-dT) X poly(dA-dT) showed no effect on the number of colonies formed [27].
  • P16 exhibited a binding preference for single strand DNA, poly(dT), and poly(dC) in comparison to double strand DNA, poly(U), or poly[d(A-T)] [28].
  • Finally, the optimised system was successfully tested on the nucleotide mixture solution to determine the methylation state of 2'-deoxycytidine-5'-monophosphate in DNA in the search for FMR1 gene changes [29].

Analytical, diagnostic and therapeutic context of deoxycytidylic acid


  1. Crystal structure of deoxycytidylate hydroxymethylase from bacteriophage T4, a component of the deoxyribonucleoside triphosphate-synthesizing complex. Song, H.K., Sohn, S.H., Suh, S.W. EMBO J. (1999) [Pubmed]
  2. Nucleotide sequence of cloned cDNAs encoding human preproparathyroid hormone. Hendy, G.N., Kronenberg, H.M., Potts, J.T., Rich, A. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  3. Cloning, sequence analysis, and expression of the bacteriophage T4 cd gene. Maley, G.F., Duceman, B.W., Wang, A.M., Martinez, J., Maley, F. J. Biol. Chem. (1990) [Pubmed]
  4. Kinetic interaction of human immunodeficiency virus type 1 reverse transcriptase with the antiviral tetrahydroimidazo[4,5,1-jk]-[1,4]-benzodiazepine-2-(1H)-thione compound, R82150. Frank, K.B., Noll, G.J., Connell, E.V., Sim, I.S. J. Biol. Chem. (1991) [Pubmed]
  5. Deoxycytidylate deaminase from Bacillus subtilis. Purification, characterization, and physiological function. Møllgaard, H., Neuhard, J. J. Biol. Chem. (1978) [Pubmed]
  6. Dependence of DNA helix flexibility on base composition. Hogan, M., LeGrange, J., Austin, B. Nature (1983) [Pubmed]
  7. Atypical methylation of the interleukin-8 gene correlates strongly with the metastatic potential of breast carcinoma cells. De Larco, J.E., Wuertz, B.R., Yee, D., Rickert, B.L., Furcht, L.T. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  8. Human TLR9 confers responsiveness to bacterial DNA via species-specific CpG motif recognition. Bauer, S., Kirschning, C.J., Häcker, H., Redecke, V., Hausmann, S., Akira, S., Wagner, H., Lipford, G.B. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  9. Dimeric structure of a human apolipoprotein B mRNA editing protein and cloning and chromosomal localization of its gene. Lau, P.P., Zhu, H.J., Baldini, A., Charnsangavej, C., Chan, L. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  10. Deoxycytidylate aminohydrolase activity in the Novikoff hepatoma is dependent on the localization of the tumor. Sheid, B. Oncology (1990) [Pubmed]
  11. Mutagenesis by alkylating agents: coding properties for DNA polymerase of poly (dC) template containing 3-methylcytosine. Boiteux, S., Laval, J. Biochimie (1982) [Pubmed]
  12. Molecular cloning of human gastrin cDNA: evidence for evolution of gastrin by gene duplication. Boel, E., Vuust, J., Norris, F., Norris, K., Wind, A., Rehfeld, J.F., Marcker, K.A. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  13. cDNA sequence of a new chicken embryonic rho-globin. Roninson, I.B., Ingram, V.M. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  14. Mammalian endonuclease, DNase V. Purification and properties of enzyme of calf thymus. Wang, E.C., Furth, J.J. J. Biol. Chem. (1977) [Pubmed]
  15. Complete amino acid sequence of an allosteric enzyme, T2 bacteriophage deoxycytidylate deaminase. Maley, G.F., Guarino, D.U., Maley, F. J. Biol. Chem. (1983) [Pubmed]
  16. Role of deoxycytidylate deaminase in deoxyribonucleotide synthesis in bacteriophage T4 DNA replication. Chiu, C.S., Ruettinger, T., Flanegan, J.B., Greenberg, G.R. J. Biol. Chem. (1977) [Pubmed]
  17. Stimulation of human neuroblastoma DNA polymerase alpha and primase activities by a protein factor isolated from rat liver chromatin. Takada, S., Torres-Rosado, A., Ray, S., Basu, S. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  18. Purification of a primase activity associated with DNA polymerase alpha from HeLa cells. Gronostajski, R.M., Field, J., Hurwitz, J. J. Biol. Chem. (1984) [Pubmed]
  19. Formation of thymidine kinase and deoxycytidylate deaminase in synchronized cultures of chinese hamster cells temperature-sensitive for DNA synthesis. Kit, S., Jorgensen, G.N. J. Cell. Physiol. (1976) [Pubmed]
  20. Overcoming inclusion body formation in a high-level expression system. Moore, J.T., Uppal, A., Maley, F., Maley, G.F. Protein Expr. Purif. (1993) [Pubmed]
  21. On the molecular basis of transition mutations. Frequency of forming 2-aminopurine-cytosine base mispairs in the G X C----A X T mutational pathway by T4 DNA polymerase in vitro. Mhaskar, D.N., Goodman, M.F. J. Biol. Chem. (1984) [Pubmed]
  22. Structural changes in the T4 gene 32 protein induced by DNA polynucleotides. Williams, K.R., Konigsberg, W. J. Biol. Chem. (1978) [Pubmed]
  23. The antibiotic bicyclomycin affects the secondary RNA binding site of Escherichia coli transcription termination factor Rho. Magyar, A., Zhang, X., Kohn, H., Widger, W.R. J. Biol. Chem. (1996) [Pubmed]
  24. Processivity and kinetics of the reaction of exonuclease I from Escherichia coli with polydeoxyribonucleotides. Brody, R.S., Doherty, K.G., Zimmerman, P.D. J. Biol. Chem. (1986) [Pubmed]
  25. Poly(dG).poly(dC) at neutral and alkaline pH: the formation of triple stranded poly(dG).poly(dG).poly(dC). Marck, C., Thiele, D. Nucleic Acids Res. (1978) [Pubmed]
  26. Transcriptional control of T4 coliphage-specific genes 30, 42, 43, rIIA, rIIB, and e. Witmer, H., Baros, A., Forbes, J., Padnos, D., Maricondia, W., Weiner, M. J. Gen. Virol. (1976) [Pubmed]
  27. Inhibition of the herpes simplex virus thymidine kinase gene transfection in Ltk- cells by potential Z-DNA forming polymers. Banerjee, R., Carothers, A.M., Grunberger, D. Nucleic Acids Res. (1985) [Pubmed]
  28. Structural and functional studies of the rat mitochondrial single strand DNA binding protein P16. Hoke, G.D., Pavco, P.A., Ledwith, B.J., Van Tuyle, G.C. Arch. Biochem. Biophys. (1990) [Pubmed]
  29. High-performance liquid chromatographic determination of deoxycytidine monophosphate and methyldeoxycytidine monophosphate for DNA demethylation monitoring: experimental design and artificial neural networks optimisation. Havlis, J., Madden, J.E., Revilla, A.L., Havel, J. J. Chromatogr. B Biomed. Sci. Appl. (2001) [Pubmed]
  30. Roles of Cys148 and Asp179 in catalysis by deoxycytidylate hydroxymethylase from bacteriophage T4 examined by site-directed mutagenesis. Graves, K.L., Butler, M.M., Hardy, L.W. Biochemistry (1992) [Pubmed]
  31. Crystallization and preliminary X-ray crystallographic analysis of deoxycytidylate hydroxymethylase from bacteriophage T4. Sohn, S.H., Song, H.K., Min, K., Cho, S.J., Moon, J., Lee, J.Y., Ahn, H.J., Chang, C., Kim, H.J., Suh, S.W. Acta Crystallogr. D Biol. Crystallogr. (1999) [Pubmed]
  32. Deoxypyrimidine cluster mediates the priming by calf thymus DNA primase subunit. Suzuki, M., Izuta, S., Savoysky, E., Sakurai, T., Simbulan, C., Tatebe, M., Kojima, K., Yoshida, S. Biochem. Mol. Biol. Int. (1993) [Pubmed]
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