Thymidine diphosphate glucose (often abbreviated dTDP-glucose or TDP-glucose) is a nucleotide-linked sugar consisting of deoxythymidine diphosphate linked to

glucose Glucose is a simple sugar with the molecular formula . Glucose is overall 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 ...

. It is the starting compound for the syntheses of many

deoxysugar Deoxy sugars are sugars that have had a hydroxyl group replaced with a hydrogen atom. Examples include: * Deoxyribose, or 2-deoxy-D-ribose, a constituent of DNA * Fucose, or 6-deoxy-L-galactose, main component of fucoidan of brown algae, and pr ...

Biosynthesis

DTDP-glucose is produced by the enzyme

glucose-1-phosphate thymidylyltransferase In enzymology, a glucose-1-phosphate thymidylyltransferase () is an enzyme that catalyzes the chemical reaction :dTTP + alpha-D-glucose 1-phosphate \rightleftharpoons diphosphate + dTDP-glucose Thus, the two substrates of this enzyme are dTTP ...

and is synthesized from

dTTP Deoxythymidine triphosphate (dTTP) is one of the four nucleoside triphosphates that are used in the ''in vivo'' synthesis of DNA. Unlike the other deoxyribonucleoside triphosphates, thymidine triphosphate does not always contain the "deoxy" prefi ...

and

glucose-1-phosphate Glucose 1-phosphate (also called cori ester) is a glucose molecule with a phosphate group on the 1'-carbon. It can exist in either the α- or β-anomeric form. Reactions of α-glucose 1-phosphate Catabolic In glycogenolysis, it is the direct pro ...

Pyrophosphate In chemistry, pyrophosphates are phosphorus oxyanions that contain two phosphorus atoms in a P–O–P linkage. A number of pyrophosphate salts exist, such as disodium pyrophosphate (Na2H2P2O7) and tetrasodium pyrophosphate (Na4P2O7), among other ...

is a byproduct of the reaction.

Uses within the cell

DTDP-glucose goes on to form a variety of compounds in

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 ...

. Many bacteria utilize dTDP-glucose to form exotic sugars that are incorporated into their

lipopolysaccharide Lipopolysaccharides (LPS) are large molecules consisting of a lipid and a polysaccharide that are bacterial toxins. They are composed of an O-antigen, an outer core, and an inner core all joined by a covalent bond, and are found in the outer m ...

s or into

secondary metabolites Secondary metabolites, also called specialised metabolites, toxins, secondary products, or natural products, are organic compounds produced by any lifeform, e.g. bacteria, fungi, animals, or plants, which are not directly involved in the nor ...

such as

antibiotics An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention o ...

. 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 The enzyme dTDP-glucose 4,6-dehydratase () catalysis, catalyzes the chemical reaction :Thymidine diphosphate glucose, dTDP-glucose \rightleftharpoons dTDP-4-dehydro-6-deoxy-D-glucose + H2O Structure and mechanism of action The first protein s ...

, producing dTDP-4-keto-6-deoxy-glucose.

References

{{Nucleotide sugars Biochemistry Nucleotides Monosaccharides