Thymidine diphosphate glucose

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]

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
Properties
C16H26N2O16P2
Molar mass 564.330 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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 & 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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.