deoxycytidine monophosphate


Summary: Deoxycytidine (dihydrogen phosphate). A deoxycytosine nucleotide containing one phosphate group esterified to the deoxyribose moiety in the 2'-,3'- or 5- positions.

Top Publications

  1. Peghini P, Zahner R, Kuster H, Schott H, Schwendener R. In vitro anti-human immunodeficiency virus and anti-hepatitis B virus activities and pharmacokinetic properties of heterodinucleoside phosphates containing AZT or ddC. Antivir Chem Chemother. 1998;9:117-26 pubmed
    ..Considering the antiviral potency and the favourable pharmacokinetic properties of the heterodimers, these compounds merit further exploration as antiviral drugs. ..
  2. Feng J, Anderson K. Mechanistic studies examining the efficiency and fidelity of DNA synthesis by the 3TC-resistant mutant (184V) of HIV-1 reverse transcriptase. Biochemistry. 1999;38:9440-8 pubmed
  3. Liu L, Santi D. Exclusion of 2'-deoxycytidine 5'-monophosphate by asparagine 229 of thymidylate synthase. Biochemistry. 1993;32:9263-7 pubmed
    ..We speculate that exclusion of cytosine versus uracil by Asn or Gln may account for specificity observed in other protein-pyrimidine interactions. ..
  4. McIntosh E, Haynes R. Isolation of a Saccharomyces cerevisiae mutant strain deficient in deoxycytidylate deaminase activity and partial characterization of the enzyme. J Bacteriol. 1984;158:644-9 pubmed
    ..The auxotrophic requirement of dcd1 dmp1 tup7 strains also can be satisfied by exogenous dTMP but not deoxyuridine. ..
  5. Farrer B, Thorp H. Redox pathways in DNA oxidation: kinetic studies of guanine and sugar oxidation by para-substituted derivatives of oxoruthenium(IV). Inorg Chem. 2000;39:44-9 pubmed
    ..The selectivity of cleavage in duplex and single-stranded DNA was not a strong function of the substituents on the metal complex. ..
  6. Les A, Adamowicz L, Rode W. Modeling of reaction steps relevant to deoxyuridylate (dUMP) enzymatic methylation and thymidylate synthase mechanism-based inhibition. J Biomol Struct Dyn. 1998;15:703-15 pubmed
    ..Interaction of the pyrimidine C(4)=O group, or its modification, with the N5,10-methylenetetrahydrofolate N(10) nitrogen atom is suggested as an additional factor influencing the inhibition process. ..
  7. Thum C, Schneider C, Palma M, Santos D, Basso L. The Rv1712 Locus from Mycobacterium tuberculosis H37Rv codes for a functional CMP kinase that preferentially phosphorylates dCMP. J Bacteriol. 2009;191:2884-7 pubmed publisher
    ..Steady-state kinetics confirmed that M. tuberculosis CMK is a monomer that preferentially phosphorylates CMP and dCMP by a sequential mechanism. A plausible role for CMK is discussed. ..
  8. Swarts S, Sevilla M. Radiolysis of spin-labeled DNA: an electron spin resonance investigation. Radiat Res. 1987;112:21-35 pubmed
    ..In the presence of oxygen, there is a dramatic decrease in the loss of both the free and DNA-bound probes due to the lack of reaction of these probes with peroxyl radicals formed by the addition of molecular oxygen to DNA radicals. ..
  9. Calderone V, Forleo C, Benvenuti M, Thaller M, Rossolini G, Mangani S. A structure-based proposal for the catalytic mechanism of the bacterial acid phosphatase AphA belonging to the DDDD superfamily of phosphohydrolases. J Mol Biol. 2006;355:708-21 pubmed

More Information


  1. Rode W, Zielinski Z, Dzik J, Kulikowski T, Bretner M, Kierdaszuk B, et al. Mechanism of inhibition of mammalian tumor and other thymidylate synthases by N4-hydroxy-dCMP, N4-hydroxy-5-fluoro-dCMP, and related analogues. Biochemistry. 1990;29:10835-42 pubmed
    ..abstract truncated at 250 words)..
  2. Hsu C, Liou J, Dutschman G, Cheng Y. Phosphorylation of Cytidine, Deoxycytidine, and Their Analog Monophosphates by Human UMP/CMP Kinase Is Differentially Regulated by ATP and Magnesium. Mol Pharmacol. 2005;67:806-14 pubmed
    ..Human UMP/CMP kinase (cytidylate kinase; EC is responsible for phosphorylation of CMP, UMP, and deoxycytidine monophosphate (dCMP) and also plays an important role in the activation of pyrimidine analogs, some of which are ..
  3. Painter G, Almond M, Mao S, Liotta D. Biochemical and mechanistic basis for the activity of nucleoside analogue inhibitors of HIV reverse transcriptase. Curr Top Med Chem. 2004;4:1035-44 pubmed
    ..The results provide insight into the molecular forces and structural features that make these molecules effective inhibitors. ..
  4. Wirtz M, Stach D, Kliem H, Wiessler M, Schmitz O. Determination of the DNA methylation level in tumor cells by capillary electrophoresis and laser-induced fluorescence detection. Electrophoresis. 2004;25:839-45 pubmed
    ..After optimization of the method it was possible to determine the methylation level in 100-ng DNA samples with a standard deviation of less than 5%. ..
  5. Zhao C, Shi Y, Lin W, Wang W, Jia Z, Yao S, et al. Fast repair of the radical cations of dCMP and poly C by quercetin and rutin. Mutagenesis. 2001;16:271-5 pubmed
    ..Together with findings from our previous studies, the present results demonstrate that non-enzymatic fast repair may be a universal form of repair involving phenolic antioxidants. ..
  6. Kruszewska H, Misicka A, Chmielowiec U. Biodegradation of DNA and nucleotides to nucleosides and free bases. Farmaco. 2004;59:13-20 pubmed
    ..The mode of degradation of DNA nucleotides depended on the type of nucleotide and its concentration, but nucleic bases or their derivatives were always formed at the end of the reaction process. ..
  7. Quinn S, Doorley G, Watson G, Cowan A, George M, Parker A, et al. Ultrafast IR spectroscopy of the short-lived transients formed by UV excitation of cytosine derivatives. Chem Commun (Camb). 2007;:2130-2 pubmed
  8. Masuda Y, Kamiya K. Biochemical properties of the human REV1 protein. FEBS Lett. 2002;520:88-92 pubmed
    ..Kinetic analysis provided evidence for high affinity for dCTP with template G, suggesting that the REV1 protein is specialized for dCTP and template G. ..
  9. Nasomphan W, Tangboriboonrat P, Smanmoo S. Selective fluorescence sensing of deoxycytidine 5'-monophosphate (dCMP) employing a bis(diphenylphosphate)diimine ligand. J Fluoresc. 2011;21:187-94 pubmed publisher
    ..5?×?10(-4) M dCMP and the detection limit was 1.25?×?10(-5) M in MeCN-H(2)O (1:1, v/v). The binding ratio between BP1 and dCMP was determined to be 1:1 with the binding constant of 3.98?±?0.60?×?10(-3) M(-1). ..
  10. Jaiswal M, Lipinski L, Bohr V, Mazur S. Efficient in vitro repair of 7-hydro-8-oxodeoxyguanosine by human cell extracts: involvement of multiple pathways. Nucleic Acids Res. 1998;26:2184-91 pubmed
    ..These data suggest that the efficient repair of 8-oxodG lesions observed in human cell extracts involves more than one pathway of base excision repair. ..
  11. Klakamp S, Horrocks W. Lanthanide ion luminescence as a probe of DNA structure. 2. Non- guanine-containing oligomers and nucleotides. J Inorg Biochem. 1992;46:193-205 pubmed
  12. Bhowmick S, B R, Mishra M, Sarma M. Investigation of dissociative electron attachment to 2'-deoxycytidine-3'-monophosphate using DFT method and time dependent wave packet approach. J Chem Phys. 2012;137:064310 pubmed publisher
    ..In addition, for the first time, an indication of quantum mechanical tunneling in strand breaking is seen from the highest anionic bound vibrational state (?(5)), which may have a substantial role during DNA damage. ..
  13. Chen T, Chang C, Chou L. Sagittal plane center of mass movement strategy and joint kinetics during sit-to-walk in elderly fallers. Clin Biomech (Bristol, Avon). 2013;28:807-12 pubmed publisher
    ..Results of this study enhance our understanding on the underlying mechanisms of the altered sit-to-walk movement and could aid in developing effective screening and rehabilitation programs to prevent falling in the elderly. ..
  14. Liou J, Krishnan P, Hsieh C, Dutschman G, Cheng Y. Assessment of the effect of phosphorylated metabolites of anti-human immunodeficiency virus and anti-hepatitis B virus pyrimidine analogs on the behavior of human deoxycytidylate deaminase. Mol Pharmacol. 2003;63:105-10 pubmed
  15. Szyfter K, Hemminki K, Crane A, Watson W. Quantitative and kinetic examination of 32P-postlabeling of etheno-substituted nucleotides. Chem Biol Interact. 1991;80:99-107 pubmed
    ..The adducts are labeled efficiently at sub-femtomole levels. All the adducts were sensitive to the 3'-dephosphorylation by P1 nuclease although the guanine derivative appeared to be more resistant than the two other adducts...
  16. Ramsahoye B. Measurement of genome-wide DNA cytosine-5 methylation by reversed-phase high-pressure liquid chromatography. Methods Mol Biol. 2002;200:17-27 pubmed
  17. Bianchi V, Pontis E, Reichard P. Regulation of pyrimidine deoxyribonucleotide metabolism by substrate cycles in dCMP deaminase-deficient V79 hamster cells. Mol Cell Biol. 1987;7:4218-24 pubmed
    ..In contrast, the balance of the deoxyuridine/dUMP cycle was shifted towards the nucleotide, facilitating import of extracellular deoxynucleosides. ..
  18. Liou J, Lai H, Hsu C, Chang W, Hsieh M, Huang Y, et al. Modulation of human UMP/CMP kinase affects activation and cellular sensitivity of deoxycytidine analogs. Biochem Pharmacol. 2010;79:381-8 pubmed publisher
    ..This study indicates that the second step enzyme (UMP/CMPK) is responsible for the phosphorylation of pyrimidine analogs and also has an impact on cellular sensitivity to these analogs in those cell lines. ..
  19. Ray A, Schinazi R, Murakami E, Basavapathruni A, Shi J, Zorca S, et al. Probing the mechanistic consequences of 5-fluorine substitution on cytidine nucleotide analogue incorporation by HIV-1 reverse transcriptase. Antivir Chem Chemother. 2003;14:115-25 pubmed
  20. Dyrkheeva N, Khodyreva S, Lavrik O. [Quantitative parameters of the 3'-5'-exonuclease reaction of human apurinic/apyrimidinic endonuclease 1 and DNA with single-strand breaks containing dYMP or their modified analogues]. Bioorg Khim. 2008;34:210-9 pubmed
    ..The English version of the paper: Russian Journal of Bioorganic Chemistry, 2008, vol. 34, no. 2; see also ..
  21. Wang W, Sevilla M. Reaction of cysteamine with individual DNA base radicals in gamma-irradiated nucleotides at low temperature. Int J Radiat Biol. 1994;66:683-95 pubmed
    ..This species, S(A)., is also found to react with cysteamine or its disulfide radical anion. Analyses performed in the presence and absence of a thiol are found to allow for a clear separation of oxidative and reductive pathways. ..
  22. Kim N, Mudrak S, Jinks Robertson S. The dCMP transferase activity of yeast Rev1 is biologically relevant during the bypass of endogenously generated AP sites. DNA Repair (Amst). 2011;10:1262-71 pubmed publisher
    ..These results demonstrate that the catalytic activity of Rev1 is biologically relevant and is required specifically for dCMP insertion during the bypass of endogenous AP sites. ..
  23. Shibutani S, Dasaradhi L. Miscoding potential of tamoxifen-derived DNA adducts: alpha-(N2-deoxyguanosinyl)tamoxifen. Biochemistry. 1997;36:13010-7 pubmed
    ..We conclude that dG-N2-tamoxifen adducts have high miscoding potentials. ..
  24. Zuo Z, Yao S, Luo J, Wang W, Zhang J. Laser photolysis of cytosine, cytidine and dCMP in aqueous solution. J Photochem Photobiol B. 1992;15:215-22 pubmed
    ..Accordingly, a series of kinetic parameters have also been obtained. ..
  25. Zhang Y, Wu X, Rechkoblit O, Geacintov N, Taylor J, Wang Z. Response of human REV1 to different DNA damage: preferential dCMP insertion opposite the lesion. Nucleic Acids Res. 2002;30:1630-8 pubmed
    ..These results suggest that human REV1 is a specialized DNA polymerase that may contribute to dCMP insertion opposite many types of DNA damage during lesion bypass. ..
  26. Fude F, Jin Z, Haixin L, Mingjia T. Study on GMA-DNA adducts. Chin Med Sci J. 1999;14:1-6 pubmed
    ..Formation of GMA-DNA adducts is an important molecular event in gene mutation and cell transformation induced by GMA. ..
  27. Huang P, Chubb S, Hertel L, Grindey G, Plunkett W. Action of 2',2'-difluorodeoxycytidine on DNA synthesis. Cancer Res. 1991;51:6110-7 pubmed
    ..Our results demonstrate qualitative and quantitative differences in the molecular actions of dFdC and arabinosylcytosine on DNA metabolism, but are consistent with an important role for such incorporation in the toxicity of dFdC. ..
  28. Tellez Sanz R, Bernier Villamor V, García Fuentes L, Gonzalez Pacanowska D, Baron C. Thermodynamic characterization of the binding of dCMP to the Asn229Asp mutant of thymidylate synthase. FEBS Lett. 1997;409:385-90 pubmed
    ..83 +/- 0.02 kJ K(-1) per mol of dCMP bound. ..
  29. Bhaskaran R, Sarma M. Effect of quantum tunneling on single strand breaks in a modeled gas phase cytidine nucleotide induced by low energy electron: a theoretical approach. J Chem Phys. 2013;139:045103 pubmed publisher
  30. Bertrand T, Briozzo P, Assairi L, Ofiteru A, Bucurenci N, Munier Lehmann H, et al. Sugar specificity of bacterial CMP kinases as revealed by crystal structures and mutagenesis of Escherichia coli enzyme. J Mol Biol. 2002;315:1099-110 pubmed publisher
    ..This is the first experimental evidence of a catalytic role involving the characteristic insert of bacterial CMP kinases. Furthermore, this role concerns only dCMP phosphorylation, a feature of this family of enzymes...
  31. Zou Z, Ding Q, Ou L, Yan B. Efficient production of deoxynucleoside-5'-monophosphates using deoxynucleoside kinase coupled with a GTP-regeneration system. Appl Microbiol Biotechnol. 2013;97:9389-95 pubmed publisher
    ..The high yield indicated that this process of biosynthesis of 5'-dAMP, 5'-dDAMP, or 5'-dCMP was efficient and economical, and this one-pot system may also potentially be used for the preparation of other types of 5'-dNMPs. ..
  32. Tsutsui M, Matsubara K, Ohshiro T, Furuhashi M, Taniguchi M, Kawai T. Electrical detection of single methylcytosines in a DNA oligomer. J Am Chem Soc. 2011;133:9124-8 pubmed publisher
    ..We also demonstrate statistical identifications of methylcytosines in an oligonucleotide by tunneling current. This result suggests a possible use of the transverse electron-transport method for a methylation level analysis. ..
  33. Jayanth N, Puranik M. Methylation stabilizes the imino tautomer of dAMP and amino tautomer of dCMP in solution. J Phys Chem B. 2011;115:6234-42 pubmed publisher
    ..We find that contrary to the general assumption, 1-me-dAMP is present in its neutral imino form at physiological pH and 3-me-dCMP is in the amino form. ..
  34. Mas A, Vázquez Alvarez B, Domingo E, Menendez Arias L. Multidrug-resistant HIV-1 reverse transcriptase: involvement of ribonucleotide-dependent phosphorolysis in cross-resistance to nucleoside analogue inhibitors. J Mol Biol. 2002;323:181-97 pubmed
    ..This proposal could explain why insertion-containing HIV-1 variants have been detected in the absence of AZT, during d4T treatment. ..
  35. Jost J, Thiry S, Siegmann M. 5-Methyldeoxycytidine monophosphate deaminase and 5-methylcytidyl-DNA deaminase activities are present in human mature sperm cells. FEBS Lett. 2002;519:128-34 pubmed
    ..The enzyme requires no divalent cations and has a Km of 1.4 x 10(-7) M for 5-mdCMP and a Vmax of 7 x 10(-11) mol/h/microg protein. The possible biological implications of the deaminase's activities in the present system are discussed. ..
  36. Chou K, Kukhanova M, Cheng Y. A novel action of human apurinic/apyrimidinic endonuclease: excision of L-configuration deoxyribonucleoside analogs from the 3' termini of DNA. J Biol Chem. 2000;275:31009-15 pubmed
    ..This discovery suggests that APE1 could be critical for the activity of l-OddC or other l-nucleoside analogs and may play additional important roles in cells that were not previously known. ..
  37. Hoes I, Lemiere F, Van Dongen W, Vanhoutte K, Esmans E, Van Bockstaele D, et al. Analysis of melphalan adducts of 2'-deoxynucleotides in calf thymus DNA hydrolysates by capillary high-performance liquid chromatography-electrospray tandem mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999;736:43-59 pubmed
    ..The most important adduct found was identified as the N-7 alklylated dGMP adduct. The alkylated dinucleotides were identified as a pdApdT/melphalan and pdGpdC/melphalan the latter being the most important. ..
  38. Holliday R, Ho T. Gene silencing and endogenous DNA methylation in mammalian cells. Mutat Res. 1998;400:361-8 pubmed
    ..It seems that 5-methyldCMP deaminase can be down-regulated in transformed cells, and this can promote de novo methylation by incorporation of 5-methyldCTP derived from 5-methyldCMP. ..
  39. Starikov E, Pedash Y. Theoretical analysis of deoxycytidine-5'-phosphate protonation. Biopolymers. 1990;30:349-55 pubmed
    ..The conclusion has been drawn that the semiempirical quantum-chemical CNDO/2 technique is applicable to the mononucleotide studies. ..
  40. Chen C, Venkatachalam T, Zhu Z, Uckun F. In vivo pharmacokinetics and metabolism of anti-human immunodeficiency virus agent D4T-5'-[p-bromophenyl methoxyalaninyl phosphate] (SAMPIDINE) in mice. Drug Metab Dispos. 2001;29:1035-41 pubmed
    ..8 min) was markedly longer than the elimination half-life of ala-d4T-MP given intravenously (38.9 min). Following oral administration of HI-113, the elimination half-lives of ala-d4T-MP (56.1 min) and d4T (102.6 min) were also prolonged. ..
  41. Felczak K, Miazga A, Poznanski J, Bretner M, Kulikowski T, Dzik J, et al. 5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity. J Med Chem. 2000;43:4647-56 pubmed
    ..While FdUMP and 6a showed a higher affinity and greater inactivation power with the parental cell than FdUrd-resistant cell enzyme, an opposite relationship could be seen with 5-hydroxymethyl-dUMP. ..
  42. Petroselli G, Dantola M, Cabrerizo F, Lorente C, Braun A, Oliveros E, et al. Quenching of the fluorescence of aromatic pterins by deoxynucleotides. J Phys Chem A. 2009;113:1794-9 pubmed publisher
    ..Possible mechanisms for the quenching of fluorescence of pterin derivatives by the different nucleotides are discussed. ..
  43. Guo D, Xie Z, Shen H, Zhao B, Wang Z. Translesion synthesis of acetylaminofluorene-dG adducts by DNA polymerase zeta is stimulated by yeast Rev1 protein. Nucleic Acids Res. 2004;32:1122-30 pubmed
    ..Consistent with the in vitro results, both Polzeta and Rev1 were found to be equally important for error-prone translesion synthesis across from AAF-dG DNA adducts in yeast cells...
  44. Vig R, Venkatachalam T, Uckun F. D4T-5'-[p-bromophenyl methoxyalaninyl phosphate] as a potent and non-toxic anti-human immunodeficiency virus agent. Antivir Chem Chemother. 1998;9:445-8 pubmed
  45. Vaishnav Y, Antony A. Binding of deoxyadenylate and deoxycytidylate antibodies to double-stranded DNA. Biochem Biophys Res Commun. 1988;154:118-23 pubmed
    ..The antibodies did not react with tRNA and rRNA. These antibodies were also shown to react with supercoiled and relaxed forms of pBR322 DNA as demonstrated by gel retardation assay. ..
  46. Song H, Sohn S, Suh S. Crystal structure of deoxycytidylate hydroxymethylase from bacteriophage T4, a component of the deoxyribonucleoside triphosphate-synthesizing complex. EMBO J. 1999;18:1104-13 pubmed
    ..On the basis of sequence comparison and crystal packing analysis, a hypothetical model for the interaction between T4 deoxycytidylate hydroxymethylase and T4 thymidylate synthase in the dNTP-synthesizing complex has been built. ..
  47. Ludwiczak J, Maj P, Wilk P, FrÄ…czyk T, Ruman T, Kierdaszuk B, et al. Phosphorylation of thymidylate synthase affects slow-binding inhibition by 5-fluoro-dUMP and N(4)-hydroxy-dCMP. Mol Biosyst. 2016;12:1333-41 pubmed publisher
    ..Inhibition of the phosphorylated enzyme by N(4)-hydroxy-dCMP was found to be strongly dependent on [Mg(2+)], cations demonstrated previously to also influence the activity of endogenous mouse TS isolated from tumour cells. ..
  48. Benevides J, Kang C, Thomas G. Raman signature of the four-stranded intercalated cytosine motif in crystal and solution structures of DNA deoxycytidylates d(CCCT) and d(C8). Biochemistry. 1996;35:5747-55 pubmed
    ..The significance of these results for probing solution conformations of telomeric DNA sequences is also considered. ..
  49. Sorokin V, Valeev V, Gladchenko G, Sysa I, Blagoi Y, Volchok I. Interaction of bivalent copper, nickel, manganese ions with native DNA and its monomers. J Inorg Biochem. 1996;63:79-98 pubmed
    ..No transformations of this kind of helix-coil transitions are caused by manganese and nickel up to concentrations 4 X 10(-2) M. ..
  50. Wolfe A, Smith T, Meehan T. Benzo[a]pyrene diol epoxide forms covalent adducts with deoxycytidylic acid by alkylation at both exocyclic amino N(4) and ring imino N-3 positions. Chem Res Toxicol. 2004;17:476-91 pubmed
    ..Molecular modeling shows that the conformers result from two low-energy conformations of very similar energies with the pyrimidine in opposite orientations, separated by significant barriers to rotation of the uracil moiety. ..
  51. Tan M, Xu J, Li Z, Lei H, Zuo J. [Study on GMA-DNA adducts in vivo]. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 1999;21:444-9 pubmed
    ..N3-methacrylate-2-hdroxypropyl-deoxycytidine monophosphate was found in kidney, liver and white blood cells...
  52. Evans F, Levine R. NMR study of stacking interactions and conformational adjustments in the dinucleotide-carcinogen adduct 2'-deoxycytidylyl-(3----5)-2'-deoxy-8-(N-fluoren-2-ylac etamido)guanosi ne. Biochemistry. 1988;27:3046-55 pubmed
    ..Such structures could explain the relatively rapid rate of repair and the frame-shift mutations of this type of adduct. ..
  53. Monaghan A, Hay R. Pyridoxal 5'-phosphate inhibition of adenovirus DNA polymerase. J Biol Chem. 1996;271:24242-8 pubmed
    ..Thus, it is likely that both the dCMP transfer activity required for initiation and DNA polymerase activity are carried out at the same site of the enzyme. ..