Thymidine diphosphate glucose

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Thymidine diphosphate glucose
Thymidine diphosphate glucose.png
Preferred IUPAC name
O1-{[(2R,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(3H)-yl)oxolan-2-yl]methyl} O3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen diphosphate
Other names
TDP-glucose; dTDP-glucose
3D model (JSmol)
PubChem CID
  • 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 Yes check.svgY
  • 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
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).
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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]



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]

Related Research Articles

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Adenosine triphosphate (ATP) is an organic compound and hydrotrope that provides energy to drive many processes in living cells, such as muscle contraction, nerve impulse propagation, condensate dissolution, and chemical synthesis. Found in all known forms of life, ATP is often referred to as the "molecular unit of currency" of intracellular energy transfer. When consumed in metabolic processes such as cellular respiration, it converts either to adenosine diphosphate (ADP) or to adenosine monophosphate (AMP). Other processes regenerate ATP so that the human body recycles its own body weight equivalent in ATP each day. It is also a precursor to DNA and RNA, and is used as a coenzyme.

Glycolysis Metabolic pathway

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Adenosine diphosphate Chemical compound

Adenosine diphosphate (ADP), also known as adenosine pyrophosphate (APP), is an important organic compound in metabolism and is essential to the flow of energy in living cells. ADP consists of three important structural components: a sugar backbone attached to adenine and two phosphate groups bonded to the 5 carbon atom of ribose. The diphosphate group of ADP is attached to the 5’ carbon of the sugar backbone, while the adenine attaches to the 1’ carbon.

Glycosyltransferase Class of enzymes that catalyze the transfer of glycosyl groups to an acceptor

Glycosyltransferases are enzymes that establish natural glycosidic linkages. They catalyze the transfer of saccharide moieties from an activated nucleotide sugar to a nucleophilic glycosyl acceptor molecule, the nucleophile of which can be oxygen- carbon-, nitrogen-, or sulfur-based.

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Uridine diphosphate glucose Chemical compound

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In enzymology, a dTDP-galactose 6-dehydrogenase (EC is an enzyme that catalyzes the chemical reaction

dTDP-4-dehydrorhamnose 3,5-epimerase

In enzymology, a dTDP-4-dehydrorhamnose 3,5-epimerase is an enzyme that catalyzes the chemical reaction

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Guanosine diphosphate mannose Chemical compound

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Glucose-1-phosphate thymidylyltransferase

In enzymology, a glucose-1-phosphate thymidylyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, an UTP—hexose-1-phosphate uridylyltransferase is an enzyme that catalyzes the chemical reaction

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Cytidine diphosphate glucose, often abbreviated CDP-glucose, is a nucleotide-linked sugar consisting of cytidine diphospahte and glucose.

DTDP-4-amino-4,6-dideoxy-D-glucose acyltransferase is an enzyme with systematic name acetyl-CoA:dTDP-4-amino-4,6-dideoxy-alpha-D-glucose N-acetyltransferase. This enzyme catalyses the following chemical reaction

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  1. 1 2 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.