Uridine diphosphate galactose

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Uridine diphosphate galactose
UDP-Galactose.svg
Names
IUPAC name
Uridine 5′-(α-D-galactopyranosyl 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,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen diphosphate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSH Uridine+diphosphate+galactose
PubChem CID
UNII
  • InChI=1S/C9H12N2O6.C6H14O12P2/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16;7-1-3(9)5(10)6(18-20(14,15)16)4(2-8)17-19(11,12)13/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16);2-7,9-10H,1H2,(H2,11,12,13)(H2,14,15,16)/p-4/t4-,6-,7-,8-;3-,4+,5+,6-/m11/s1 Yes check.svgY
    Key: UYLAOKYVSPTOGT-UESRDHDISA-J Yes check.svgY
  • InChI=1/C9H12N2O6.C6H14O12P2/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16;7-1-3(9)5(10)6(18-20(14,15)16)4(2-8)17-19(11,12)13/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16);2-7,9-10H,1H2,(H2,11,12,13)(H2,14,15,16)/p-4/t4-,6-,7-,8-;3-,4+,5+,6-/m11/s1
    Key: UYLAOKYVSPTOGT-HUYLZDLQBS
  • [H]OC([H])([H])[C@]1([H])O[C@]([H])(O[P@@](=O)(O[H])O[P@](=O)(O[H])OC([H])([H])[C@]2([H])O[C@@]([H])(N3C([H])=C([H])C(=O)N([H])C3=O)[C@]([H])(O[H])[C@@]2([H])O[H])[C@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Uridine diphosphate galactose ( UDP-galactose ) is an intermediate in the production of polysaccharides. [1] It is important in nucleotide sugars metabolism, and is the substrate for the transferase B4GALT5.

Contents

Sugar metabolism

UDP-Galactose is especially relevant in glycolysis. It is derived from galactose an epimer of glucose, and via the Leloir Pathway, it is used be used as a precursor for the metabolism of glucose into pyruvate. [2] When lactose is hydrolyzed, D-Galactose enters the liver via the bloodstream. There, galactokinase phosphorylates it to galactose-1-phosphate using ATP. This compound then engages in a "ping-pong" reaction with UDP-Glucose, catalyzed by uridylyltransferase, yielding glucose-1-phosphate and UDP-Galactose. This glucose-1-phosphate feeds into glycolysis, while UDP-Galactose undergoes epimerization to regenerate UDP-Glucose. [3]

transforming galatose (1) to glucose for the glycolysis. Galactose-1-phosphate (2), UDP-glucose (3), UDP-galatose (4) ; Glucose 1-phosphate (5); Glucose 6-phosphate (6). Galactokinase (GK), Galactose-1-phosphate uridylyltransferase (GALT), UDP-glucose 4-epimerase (UGE), phosphoglucomutase (PGM) Galactose in glycolysis.svg
transforming galatose (1) to glucose for the glycolysis. Galactose-1-phosphate (2), UDP-glucose (3), UDP-galatose (4) ; Glucose 1-phosphate (5); Glucose 6-phosphate (6). Galactokinase (GK), Galactose-1-phosphate uridylyltransferase (GALT), UDP-glucose 4-epimerase (UGE), phosphoglucomutase (PGM)

See also

Related Research Articles

<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">Adenosine diphosphate</span> 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.

<span class="mw-page-title-main">Anabolism</span> Metabolic pathways to build molecules

Anabolism is the set of metabolic pathways that construct macromolecules like DNA or RNA from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catabolism is the breaking-down aspect. Anabolism is usually synonymous with biosynthesis.

<span class="mw-page-title-main">Glycogenolysis</span> Breakdown of glycogen

Glycogenolysis is the breakdown of glycogen (n) to glucose-1-phosphate and glycogen (n-1). Glycogen branches are catabolized by the sequential removal of glucose monomers via phosphorolysis, by the enzyme glycogen phosphorylase.

Carbohydrate metabolism is the whole of the biochemical processes responsible for the metabolic formation, breakdown, and interconversion of carbohydrates in living organisms.

<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">Glucose 6-phosphate</span> Chemical compound

Glucose 6-phosphate is a glucose sugar phosphorylated at the hydroxy group on carbon 6. This dianion is very common in cells as the majority of glucose entering a cell will become phosphorylated in this way.

In organic chemistry, a tetrose is a monosaccharide with 4 carbon atoms. They have either an aldehyde functional group in position 1 (aldotetroses) or a ketone group in position 2 (ketotetroses).

Bioenergetics is a field in biochemistry and cell biology that concerns energy flow through living systems. This is an active area of biological research that includes the study of the transformation of energy in living organisms and the study of thousands of different cellular processes such as cellular respiration and the many other metabolic and enzymatic processes that lead to production and utilization of energy in forms such as adenosine triphosphate (ATP) molecules. That is, the goal of bioenergetics is to describe how living organisms acquire and transform energy in order to perform biological work. The study of metabolic pathways is thus essential to bioenergetics.

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

Galactosamine is a hexosamine derived from galactose with the molecular formula C6H13NO5. This amino sugar is a constituent of some glycoprotein hormones such as follicle-stimulating hormone (FSH) and luteinizing hormone (LH).

<span class="mw-page-title-main">Nucleic acid metabolism</span> Process

Nucleic acid metabolism is a collective term that refers to the variety of chemical reactions by which nucleic acids are either synthesized or degraded. Nucleic acids are polymers made up of a variety of monomers called nucleotides. Nucleotide synthesis is an anabolic mechanism generally involving the chemical reaction of phosphate, pentose sugar, and a nitrogenous base. Degradation of nucleic acids is a catabolic reaction and the resulting parts of the nucleotides or nucleobases can be salvaged to recreate new nucleotides. Both synthesis and degradation reactions require multiple enzymes to facilitate the event. Defects or deficiencies in these enzymes can lead to a variety of diseases.

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

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

<span class="mw-page-title-main">Xylulose 5-phosphate</span> Chemical compound

D-Xylulose 5-phosphate (D-xylulose-5-P) is an intermediate in the pentose phosphate pathway. It is a ketose sugar formed from ribulose-5-phosphate by ribulose-5-phosphate epimerase. In the non-oxidative branch of the pentose phosphate pathway, xylulose-5-phosphate acts as a donor of two-carbon ketone groups in transketolase reactions.

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

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">Galactose 1-phosphate</span> Chemical compound

D-Galactose-1-phosphate is an intermediate in the intraconversion of glucose and uridine diphosphate galactose. It is formed from galactose by galactokinase.The improper metabolism of galactose-1-phosphate is a characteristic of galactosemia. The Leloir pathway is responsible for such metabolism of galactose and its intermediate, galactose-1-phosphate. Deficiency of enzymes found in this pathway can result in galactosemia; therefore, diagnosis of this genetic disorder occasionally involves measuring the concentration of these enzymes. One of such enzymes is galactose-1-phosphate uridylyltransferase (GALT). The enzyme catalyzes the transfer of a UDP-activator group from UDP-glucose to galactose-1-phosphate. Although the cause of enzyme deficiency in the Leloir pathway is still disputed amongst researchers, some studies suggest that protein misfolding of GALT, which may lead to an unfavorable conformational change that impacts its thermal stability and substrate-binding affinity, may play a role in the deficiency of GALT in Type 1 galactosemia. Increase in galactitol concentration can be seen in patients with galactosemia; putting patients at higher risk for presenile cataract.

<span class="mw-page-title-main">Deoxyuridine monophosphate</span> Chemical compound

Deoxyuridine monophosphate (dUMP), also known as deoxyuridylic acid or deoxyuridylate in its conjugate acid and conjugate base forms, respectively, is a deoxynucleotide.

<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.

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

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

<span class="mw-page-title-main">Inborn errors of carbohydrate metabolism</span> Medical condition

Inborn errors of carbohydrate metabolism are inborn error of metabolism that affect the catabolism and anabolism of carbohydrates.

<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. Los, E.; Ford, G. A. (2022). "Galactose 1 Phosphate Uridyltransferase Deficiency". StatPearls. StatPearls. PMID   28722986.
  2. Garrett, Reginald H.; Grisham, Charles M. (2017). Biochemistry (6th ed.). Boston, MA, USA: Cengage Learning. ISBN   978-1-305-57720-6.
  3. Nelson, David L.; Cox, Michael M.; Nelson, David L. (2013). Lehninger, Albert L. (ed.). Lehninger principles of biochemistry (6th ed.). Basingstoke: Macmillan Higher Education. ISBN   978-1-4292-3414-6.