Thymidine diphosphate glucose

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Thymidine diphosphate glucose
Thymidine diphosphate glucose.png
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
PubChem CID
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).
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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]

Contents

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]

Related Research Articles

Adenosine triphosphate Chemical compound

Adenosine triphosphate (ATP) is an organic compound and hydrotrope that provides energy to drive many processes in living cells, e.g. 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, 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

Glycolysis (from glycose, an older term for glucose + -lysis degradation) is the metabolic pathway that converts glucose C6H12O6, into pyruvate, CH3COCOO (pyruvic acid), and a hydrogen ion, H+. The free energy released in this process is used to form the high-energy molecules ATP (adenosine triphosphate) and NADH (reduced nicotinamide adenine dinucleotide). Glycolysis is a sequence of ten enzyme-catalyzed reactions. Most monosaccharides, such as fructose and galactose, can be converted to one of these intermediates. The intermediates may also be directly useful rather than just utilized as steps in the overall reaction. For example, the intermediate dihydroxyacetone phosphate (DHAP) is a source of the glycerol that combines with fatty acids to form fat.

Adenosine diphosphate

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 adenosine attaches to the 1’ carbon.

Pyridoxal phosphate Active form of vitamin B6

Pyridoxal phosphate (PLP, pyridoxal 5'-phosphate, P5P), the active form of vitamin B6, is a coenzyme in a variety of enzymatic reactions. The Enzyme commission has catalogued more than 140 PLP-dependent activities, corresponding to ~4% of all classified activities. The versatility of PLP arises from its ability to covalently bind the substrate, and then to act as an electrophilic catalyst, thereby stabilizing different types of carbanionic reaction intermediates.

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.

Colitose

Colitose is a mannose-derived 3,6-dideoxysugar produced by certain bacteria. It is a constituent of the lipopolysaccharide.

Uridine diphosphate glucose

Uridine diphosphate glucose is a nucleotide sugar. It is involved in glycosyltransferase reactions in metabolism.

Ribose-phosphate diphosphokinase class of enzymes

Ribose-phosphate diphosphokinase is an enzyme that converts ribose 5-phosphate into phosphoribosyl pyrophosphate (PRPP). It is classified under EC 2.7.6.1.

In enzymology, a dTDP-galactose 6-dehydrogenase (EC 1.1.1.186) is an enzyme that catalyzes the chemical reaction

dTDP-4-dehydrorhamnose 3,5-epimerase class of enzymes

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

In enzymology, a dTDP-glucose 4,6-dehydratase (EC 4.2.1.46) is an enzyme that catalyzes the chemical reaction

Nucleotide sugars metabolism

In nucleotide sugar metabolism a group of biochemicals known as nucleotide sugars act as donors for sugar residues in the glycosylation reactions that produce polysaccharides. They are substrates for glycosyltransferases. The nucleotide sugars are also intermediates in nucleotide sugar interconversions that produce some of the activated sugars needed for glycosylation reactions. Since most glycosylation takes place in the endoplasmic reticulum and golgi apparatus, there are a large family of nucleotide sugar transporters that allow nucleotide sugars to move from the cytoplasm, where they are produced, into the organelles where they are consumed.

Nucleotide sugars are the activated forms of monosaccharides. Nucleotide sugars act as glycosyl donors in glycosylation reactions. Those reactions are catalyzed by a group of enzymes called glycosyltransferases.

Guanosine diphosphate mannose

Guanosine diphosphate mannose or GDP-mannose is a nucleotide sugar that is a substrate for glycosyltransferase reactions in metabolism. This compound is a substrate for enzymes called mannosyltransferases.

In enzymology, a dTDP-4-amino-4,6-dideoxy-D-glucose transaminase is an enzyme that catalyzes the chemical reaction

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

Glucose-1-phosphate thymidylyltransferase class of enzymes

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

Cytidine diphosphate glucose

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

References

  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.