Uridine diphosphate glucose

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Uridine diphosphate glucose
UDP-Glucose.svg
Names
IUPAC name
Uridine 5′-(α-D-glucopyranosyl dihydrogen diphosphate)
Systematic IUPAC name
O1-{[(2R,3S,4R,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methyl} O3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen diphosphate
Other names
UDP-glucose
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.657 OOjs UI icon edit-ltr-progressive.svg
MeSH Uridine+Diphosphate+Glucose
PubChem CID
UNII
  • InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1 Yes check.svgY
    Key: HSCJRCZFDFQWRP-JZMIEXBBSA-N Yes check.svgY
  • InChI=1/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1
    Key: HSCJRCZFDFQWRP-JZMIEXBBBU
  • O=P(O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)(O)OP(=O)(O)OC[C@H]3O[C@@H](N2/C=C\C(=O)NC2=O)[C@H](O)[C@@H]3O
Properties
C15H24N2O17P2
Molar mass 566.302 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Uridine diphosphate glucose (uracil-diphosphate glucose, UDP-glucose ) is a nucleotide sugar. It is involved in glycosyltransferase reactions in metabolism.

Contents

Functions

UDP-glucose is used in nucleotide sugar metabolism as an activated form of glucose, a substrate for enzymes called glucosyltransferases. [1]

UDP-glucose is a precursor of glycogen and can be converted into UDP-galactose and UDP-glucuronic acid, which can then be used as substrates by the enzymes that make polysaccharides containing galactose and glucuronic acid.

UDP-glucose can also be used as a precursor of sucrose, lipopolysaccharides and glycosphingolipids.

Components

UDP-glucose consists of the pyrophosphate group, ribose, glucose, and uracil.

See also

Related Research Articles

<span class="mw-page-title-main">Uracil</span> Chemical compound of RNA

Uracil is one of the four nucleobases in the nucleic acid RNA. 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 (T). Uracil is a demethylated form of thymine.

<span class="mw-page-title-main">Uridine</span> One of the five major nucleosides in nucleic acids

Uridine (symbol U or Urd) is a glycosylated pyrimidine analog containing uracil attached to a ribose ring (or more specifically, a ribofuranose) via a β-N1-glycosidic bond. The analog is one of the five standard nucleosides which make up nucleic acids, the others being adenosine, thymidine, cytidine and guanosine. The five nucleosides are commonly abbreviated to their symbols, U, A, dT, C, and G, respectively. However, thymidine is more commonly written as 'dT' ('d' represents 'deoxy') as it contains a 2'-deoxyribofuranose moiety rather than the ribofuranose ring found in uridine. This is because thymidine is found in deoxyribonucleic acid (DNA) and usually not in ribonucleic acid (RNA). Conversely, uridine is found in RNA and not DNA. The remaining three nucleosides may be found in both RNA and DNA. In RNA, they would be represented as A, C and G whereas in DNA they would be represented as dA, dC and dG.

<span class="mw-page-title-main">Uridine triphosphate</span> Chemical compound

Uridine-5′-triphosphate (UTP) is a pyrimidine nucleoside triphosphate, consisting of the organic base uracil linked to the 1′ carbon of the ribose sugar, and esterified with tri-phosphoric acid at the 5′ position. Its main role is as substrate for the synthesis of RNA during transcription. UTP is the precursor for the production of CTP via CTP synthetase. UTP can be biosynthesized from UDP by Nucleoside Diphosphate Kinase after using the phosphate group from ATP. UDP + ATP ⇌ UTP + ADP; both UTP and ATP are energetically equal.

<span class="mw-page-title-main">Uridine diphosphate</span> Chemical compound

Uridine diphosphate, abbreviated UDP, is a nucleotide diphosphate. It is an ester of pyrophosphoric acid with the nucleoside uridine. UDP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase uracil.

Glucuronidation is often involved in drug metabolism of substances such as drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids, and bile acids. These linkages involve glycosidic bonds.

<span class="mw-page-title-main">Glucuronic acid</span> Chemical compound

Glucuronic acid is a uronic acid that was first isolated from urine. It is found in many gums such as gum arabic, xanthan, and kombucha tea and is important for the metabolism of microorganisms, plants and animals.

<span class="mw-page-title-main">UTP—glucose-1-phosphate uridylyltransferase</span>

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.,

<span class="mw-page-title-main">Uridine diphosphate galactose</span> Chemical compound

Uridine diphosphate galactose (UDP-galactose) is an intermediate in the production of polysaccharides. It is important in nucleotide sugars metabolism, and is the substrate for the transferase B4GALT5.

<span class="mw-page-title-main">Galactose-1-phosphate uridylyltransferase deficiency</span> Medical condition

Galactose-1-phosphate uridylyltransferase deficiency(classic galactosemia) is the most common type of galactosemia, an inborn error of galactose metabolism, caused by a deficiency of the enzyme galactose-1-phosphate uridylyltransferase. It is an autosomal recessive metabolic disorder that can cause liver disease and death if untreated. Treatment of galactosemia is most successful if initiated early and includes dietary restriction of lactose intake. Because early intervention is key, galactosemia is included in newborn screening programs in many areas. On initial screening, which often involves measuring the concentration of galactose in blood, classic galactosemia may be indistinguishable from other inborn errors of galactose metabolism, including galactokinase deficiency and galactose epimerase deficiency. Further analysis of metabolites and enzyme activities are needed to identify the specific metabolic error.

Uridine diphosphate <i>N</i>-acetylglucosamine Chemical compound

Uridine diphosphate N-acetylglucosamine or UDP-GlcNAc is a nucleotide sugar and a coenzyme in metabolism. It is used by glycosyltransferases to transfer N-acetylglucosamine residues to substrates. D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars. To be specific, glucosamine-6-phosphate is synthesized from fructose 6-phosphate and glutamine as the first step of the hexosamine biosynthesis pathway. The end-product of this pathway is UDP-GlcNAc, which is then used for making glycosaminoglycans, proteoglycans, and glycolipids.

In enzymology, an UDP-arabinose 4-epimerase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">UDP-glucose 4-epimerase</span> Class of enzymes

The enzyme UDP-glucose 4-epimerase, also known as UDP-galactose 4-epimerase or GALE, is a homodimeric epimerase found in bacterial, fungal, plant, and mammalian cells. This enzyme performs the final step in the Leloir pathway of galactose metabolism, catalyzing the reversible conversion of UDP-galactose to UDP-glucose. GALE tightly binds nicotinamide adenine dinucleotide (NAD+), a co-factor required for catalytic activity.

In enzymology, an UDP-glucuronate 4-epimerase is an enzyme that catalyzes the chemical reaction

In enzymology, an UDP-glucuronate 5'-epimerase is an enzyme that catalyzes the chemical reaction

In enzymology, a lipopolysaccharide 3-alpha-galactosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a glucuronate-1-phosphate uridylyltransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">UDP-glucose—hexose-1-phosphate uridylyltransferase</span>

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

<span class="mw-page-title-main">UTP—hexose-1-phosphate uridylyltransferase</span>

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

David Sidney Feingold was an American biochemist.

<span class="mw-page-title-main">Leloir pathway</span>

The Leloir pathway is a metabolic pathway for the catabolism of D-galactose. It is named after Luis Federico Leloir, who first described it.

References

  1. Rademacher T, Parekh R, Dwek R (1988). "Glycobiology". Annu Rev Biochem. 57: 785–838. doi:10.1146/annurev.bi.57.070188.004033. PMID   3052290.