Cytidine diphosphate glucose

Cytidine diphosphate glucose
Names
	IUPAC name Cytidine 5′-(α-D-glucopyranosyl trihydrogen diphosphate)
	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
Identifiers
CAS Number	2906-23-2 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	388381 ;
PubChem CID	439244;
UNII	C3MET5N4NR ;
CompTox Dashboard (EPA)	DTXSID301028840 ;
	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/s1 Key: CGPHZDRCVSLMCF-JZMIEXBBSA-N ;
	SMILES C1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O; O=P(O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)(O)OP(=O)(O)OC[C@H]3O[C@@H](N2/C=C\C(=N/C2=O)\N)[C@H](O)[C@@H]3O;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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]

Metabolism

CDP-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

↑ 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.
1 2 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. PMID 15634670.
↑ 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. PMID 7867779.

[Reeves-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.

[Liu-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.

[:0-3] 1 2 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. PMID 15634670.

[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. PMID 7867779.

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Metabolism

References