Cytidine triphosphate


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Cytidine triphosphate (CTP) is a pyrimidine nucleoside triphosphate. CTP, much like ATP, consists of a ribose sugar, and three phosphate groups. The major difference between the two molecules is the base used, which in CTP is cytosine.

Cytidine triphosphate
Skeletal formula of cytidine triphosphate as an anion (3- charge)
Space-filling model of the cytidine triphosphate molecule as an anion (4- charge)
Names
IUPAC name

Cytidine 5′-(tetrahydrogen triphosphate)

Systematic IUPAC name

O1-{[(2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methyl} tetrahydrogen triphosphate

Other names

CTP; Cytidine-5'-triphosphate

Identifiers

3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.556 Edit this at Wikidata
MeSH Cytidine+triphosphate
UNII

  • InChI=1S/C9H13N3O5.3H3O4P/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;3*1-5(2,3)4/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);3*(H3,1,2,3,4)/t4-,6-,7-,8-;;;/m1.../s1 check

    Key: NPIWPFUCEAMYFN-LLWADOMFSA-N check

  • InChI=1/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

    Key: PCDQPRRSZKQHHS-XVFCMESIBL

  • InChI=1/C9H13N3O5.3H3O4P/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;3*1-5(2,3)4/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);3*(H3,1,2,3,4)/t4-,6-,7-,8-;;;/m1.../s1

    Key: NPIWPFUCEAMYFN-LLWADOMFBY

  • c1cn(c(=O)nc1N)[C@H]2[C@@H]([C@@H]([C@H](O2)CO[P@](=O)(O)O[P@](=O)(O)OP(=O)(O)O)O)O

  • OP(O)(=O)O.OP(O)(=O)O.OP(O)(=O)O.N/C1=N/C(=O)N(/C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O

Properties
C9H16N3O14P3
Molar mass 483.156

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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CTP is a substrate in the synthesis of RNA.

CTP is a high-energy molecule similar to ATP, but its role as an energy coupler is limited to a much smaller subset of metabolic reactions. CTP is a coenzyme in metabolic reactions like the synthesis of glycerophospholipids, where it is used for activation and transfer of diacylglycerol and lipid head groups,[1] and glycosylation of proteins.

CTP acts as an inhibitor of the enzyme aspartate carbamoyltransferase, which is used in pyrimidine biosynthesis.[2]

  1. ^ Buchanan BB, Gruissem W, Jones RL (2000). Biochemistry & molecular biology of plants (1st ed.). American society of plant physiology. ISBN 978-0-943088-39-6.
  2. ^ Blackburn, G. Michael. Nucleic Acids in Chemistry and Biology. The Royal Society of Chemistry, 2006, p. 119-120.