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 564.33 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]

Thymidine diphosphate chemical compound

Thymidine diphosphate (TDP) or deoxythymidine diphosphate (dTDP) is a nucleotide diphosphate. It is an ester of pyrophosphoric acid with the nucleoside thymidine. dTDP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase thymine. Unlike the other deoxyribonucleotides, thymidine diphosphate does not always contain the "deoxy" prefix in its name.

Glucose A simple form of sugar

Glucose (also called dextrose) is a simple sugar with the molecular formula C6H12O6. Glucose is the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight. There it is used to make cellulose in cell walls, which is the most abundant carbohydrate. In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is partially stored as a polymer, in plants mainly as starch and amylopectin and in animals as glycogen. Glucose circulates in the blood of animals as blood sugar. The naturally occurring form of glucose is D-glucose, while L-glucose is produced synthetically in comparably small amounts and is of lesser importance.

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.

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

Pyrophosphate salt or ester of diphosphoric acid

In chemistry, a pyrophosphate is a phosphorus oxyanion. Compounds such as salts and esters are also called pyrophosphates. The group is also called diphosphate or dipolyphosphate, although this should not be confused with phosphates. As a food additive, diphosphates are known as E450. A number of hydrogen pyrophosphates also exist, such as Na2H2P2O7, as well as the normal pyrophosphates.

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]

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.

Lipopolysaccharide chemical compound

Lipopolysaccharides (LPS), also known as lipoglycans and endotoxins, are large molecules consisting of a lipid and a polysaccharide composed of O-antigen, outer core and inner core joined by a covalent bond; they are found in the outer membrane of Gram-negative bacteria.

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

Related Research Articles

Uracil chemical compound

Uracil is one of the four nucleobases in the nucleic acid of RNA that are represented by the letters A, G, C and U. The others are adenine (A), cytosine (C), and guanine (G). In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by thymine. Uracil is a demethylated form of thymine.

Glycosyltransferase

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 chemical compound

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

Uridine diphosphate glucose chemical compound

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

UTP—glucose-1-phosphate uridylyltransferase

UTP—glucose-1-phosphate uridylyltransferase also known as glucose-1-phosphate uridylyltransferase is an enzyme involved in carbohydrate metabolism. It synthesizes UDP-glucose from glucose-1-phosphate and UTP; i.e.,

Ribose-phosphate diphosphokinase

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

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

Guanosine diphosphate mannose chemical compound

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

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

Cytidine diphosphate glucose chemical compound

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

DTDP-3-amino-3,6-dideoxy-alpha-D-galactopyranose N,N-dimethyltransferase is an enzyme with systematic name S-adenosyl-L-methionine:dTDP-3-amino-3,6-dideoxy-alpha-D-galactopyranose 3-N,N-dimethyltransferase. This enzyme catalyses the following chemical reaction

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

DTDP-dihydrostreptose---streptidine-6-phosphate dihydrostreptosyltransferase is an enzyme with systematic name dTDP-L-dihydrostreptose:streptidine-6-phosphate dihydrostreptosyltransferase. 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.