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Cytidine diphosphate glucose

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Cytidine diphosphate glucose
Names
IUPAC name Cytidine 5′-(α-D-glucopyranosyl trihydrogen diphosphate)
Systematic IUPAC name O-{methyl} O- dihydrogen diphosphate
Other names CDP-glucose
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H25N3O16P2/c16-7-1-2-18(15(25)17-7)13-11(23)9(21)6(31-13)4-30-35(26,27)34-36(28,29)33-14-12(24)10(22)8(20)5(3-19)32-14/h1-2,5-6,8-14,19-24H,3-4H2,(H,26,27)(H,28,29)(H2,16,17,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1Key: CGPHZDRCVSLMCF-JZMIEXBBSA-N
SMILES
  • C1=CN(C(=O)N=C1N)2(((O2)COP(=O)(O)OP(=O)(O)O3((((O3)CO)O)O)O)O)O
  • O=P(O1O((O)(O)1O)CO)(O)OP(=O)(O)OC3O(N2/C=C\C(=N/C2=O)\N)(O)3O
Properties
Chemical formula C15H25N3O16P2
Molar mass 565.318 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Cytidine diphosphate glucose, often abbreviated CDP-glucose, is a nucleotide-linked sugar consisting of cytidine diphosphate and glucose. This nucleotide saccharide participates in the synthesis of deoxy sugars such as paratose and tyvelose.

Metabolism

CDP-glucose is produced from CTP and glucose-1-phosphate by the enzyme glucose-1-phosphate cytidylyltransferase.

CDP-glucose is an important metabolite in certain bacteria, which synthesize O antigens from it. CDP-glucose can also be used as a substrate for glycogenin, along its native substrate, UDP-glucose. The same is true for TDP-glucose.

References

  1. Samuel G, Reeves P (2003). "Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly". Carbohydr. Res. 338 (23): 2503–19. doi:10.1016/j.carres.2003.07.009. PMID 14670712.
  2. Xue M. He and Hung-wen Liu (2002). "Formation of unusual sugars: Mechanistic studies and biosynthetic applications". Annu Rev Biochem. 71: 701–754. doi:10.1146/annurev.biochem.71.110601.135339. PMID 12045109.
  3. ^ Koropatkin, Nicole M.; Cleland, W. Wallace; Holden, Hazel M. (March 2005). "Kinetic and Structural Analysis of α-d-Glucose-1-phosphate Cytidylyltransferase from Salmonella typhi". Journal of Biological Chemistry. 280 (11): 10774–10780. doi:10.1074/jbc.m414111200. ISSN 0021-9258.
  4. Alonso, Miriam D.; Lagzdins, Erik J.; Lomako, Joseph; Lomako, Wieslawa M.; Whelan, William J. (1995-02-13). "New and specific nucleoside diphosphate glucose substrates for glycogenin". FEBS Letters. 359 (2–3): 110–112. Bibcode:1995FEBSL.359..110A. doi:10.1016/0014-5793(95)00018-5. ISSN 0014-5793.
Types of nucleotide sugars
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