Cytidine diphosphate glucose, often abbreviated CDP-glucose, is a nucleotide-linked sugar consisting of cytidine diphosphate and glucose.[1][2] This nucleotide saccharide participates in the synthesis of deoxy sugars such as paratose and tyvelose.[3]
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Names | |
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IUPAC name
Cytidine 5′-(α-D-glucopyranosyl trihydrogen diphosphate)
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Systematic IUPAC name
O1-{[(2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methyl} O3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen diphosphate | |
Other names
CDP-glucose
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C15H25N3O16P2 | |
Molar mass | 565.318 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Metabolism
editCDP-glucose is produced from CTP and glucose-1-phosphate by the enzyme glucose-1-phosphate cytidylyltransferase.[3]
CDP-glucose is an important metabolite in certain bacteria, which synthesize O antigens from it.[3] CDP-glucose can also be used as a substrate for glycogenin, along its native substrate, UDP-glucose. The same is true for TDP-glucose.[4]
References
edit- ^ 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.
- ^ 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.
- ^ a b c 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.
- ^ 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.