Thymidine diphosphate glucose

Thymidine diphosphate glucose

Names
IUPAC name [[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-oxidophosphoryl] [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
Other names TDP-glucose; dTDP-glucose
Identifiers
CAS Number	2196-62-5
ChEBI	CHEBI:15700
ChEMBL	ChEMBL412989
ChemSpider	391476
Jmol interactive 3D	Image Image
PubChem	25202390 443210
InChI InChI=1S/C16H26N2O16P2/c1-6-3-18(16(25)17-14(6)24)10-2-7(20)9(31-10)5-30-35(26,27)34-36(28,29)33-15-13(23)12(22)11(21)8(4-19)32-15/h3,7-13,15,19-23H,2,4-5H2,1H3,(H,26,27)(H,28,29)(H,17,24,25)/t7-,8+,9+,10+,11+,12-,13+,15+/m0/s1 Key: YSYKRGRSMLTJNL-URARBOGNSA-N
SMILES CC1=CN(C(=O)NC1=O)[C@H]2C[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=C1\C(=C/N(C(=O)N1)[C@@H]2O[C@@H]([C@@H](O)C2)COP(=O)(O)OP(=O)(O)O[C@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO)C
Properties
Chemical formula	C16H26N2O16P2
Molar mass	564.33 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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Infobox references

Thymidine diphosphate glucose (often abbreviated dTDP-glucose or TDP-glucose) is a nucleotide-linked sugar consisting of deoxythymidine diphosphate linked to glucose. It is the starting compound for the syntheses of many deoxysugars.^[1]

Biosynthesis

DTDP-glucose is produced by the enzyme glucose-1-phosphate thymidylyltransferase and is synthesized from dTTP and glucose-1-phosphate. Pyrophosphate is a byproduct of the reaction.

Uses within the cell

DTDP-glucose goes on to form a variety of compounds in nucleotide sugars metabolism. Many bacteria utilize dTDP-glucose to form exotic sugars that are incorporated into their lipopolysaccharides or into secondary metabolites such as antibiotics. During the syntheses of many of these exotic sugars, dTDP-glucose undergoes a combined oxidation/reduction reaction via the enzyme dTDP-glucose 4,6-dehydratase, producing dTDP-4-keto-6-deoxy-glucose.^[1][2]

References

1. 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.
2. 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.