Cytidine diphosphate glucose

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Cytidine diphosphate glucose
Cytidine diphosphate glucose.png
Names
IUPAC name
Cytidine 5′-(α-D-glucopyranosyl trihydrogen diphosphate)
Systematic IUPAC name
O1-{[(2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-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
CDP-glucose
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C15H25N3O16P2/c16-7-1-2-18(15(25)17-7)13-11(23)9(21)6(31-13)4-30-35(26,27)34-36(28,29)33-14-12(24)10(22)8(20)5(3-19)32-14/h1-2,5-6,8-14,19-24H,3-4H2,(H,26,27)(H,28,29)(H2,16,17,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1 X mark.svgN
    Key: CGPHZDRCVSLMCF-JZMIEXBBSA-N X mark.svgN
  • C1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
  • 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(=N/C2=O)\N)[C@H](O)[C@@H]3O
Properties
C15H25N3O16P2
Molar mass 565.318 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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Cytidine diphosphate glucose, often abbreviated CDP-glucose, is a nucleotide-linked sugar consisting of cytidine diphosphate and glucose. [1] [2] This nucleotide saccharide participates in the synthesis of deoxy sugars such as paratose and tyvelose. [3]

Metabolism

CDP-glucose is produced from CTP and glucose-1-phosphate by the enzyme glucose-1-phosphate cytidylyltransferase. [3]

CDP-glucose is an important metabolite in certain bacteria, which synthesize O antigens from it. [3] CDP-glucose can also be used as a substrate for glycogenin, along its native substrate, UDP-glucose. The same is true for TDP-glucose. [4]

Related Research Articles

<span class="mw-page-title-main">Adenosine triphosphate</span> Energy-carrying molecule in living cells

Adenosine triphosphate (ATP) is a nucleotide that provides energy to drive and support many processes in living cells, such as muscle contraction, nerve impulse propagation, and chemical synthesis. Found in all known forms of life, it is often referred to as the "molecular unit of currency" for intracellular energy transfer.

A salvage pathway is a pathway in which a biological product is produced from intermediates in the degradative pathway of its own or a similar substance. The term often refers to nucleotide salvage in particular, in which nucleotides are synthesized from intermediates in their degradative pathway.

A nucleoside triphosphate is a nucleoside containing a nitrogenous base bound to a 5-carbon sugar, with three phosphate groups bound to the sugar. They are the molecular precursors of both DNA and RNA, which are chains of nucleotides made through the processes of DNA replication and transcription. Nucleoside triphosphates also serve as a source of energy for cellular reactions and are involved in signalling pathways.

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

Cytidine diphosphate, abbreviated CDP, is a nucleoside diphosphate. It is an ester of pyrophosphoric acid with the nucleoside cytidine. CDP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase cytosine.

<span class="mw-page-title-main">Glycogenin</span> Enzyme involved in converting glucose to glycogen

Glycogenin is an enzyme involved in converting glucose to glycogen. It acts as a primer, by polymerizing the first few glucose molecules, after which other enzymes take over. It is a homodimer of 37-kDa subunits and is classified as a glycosyltransferase.

<span class="mw-page-title-main">Glycogen synthase</span> Enzyme class, includes all types of glycogen/starch synthases

Glycogen synthase is a key enzyme in glycogenesis, the conversion of glucose into glycogen. It is a glycosyltransferase that catalyses the reaction of UDP-glucose and n to yield UDP and n+1.

<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">Ribose-phosphate diphosphokinase</span> 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.

CDP-4-dehydro-6-deoxyglucose reductase (EC 1.17.1.1) is an enzyme that catalyzes the chemical reaction

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.

<span class="mw-page-title-main">Guanosine diphosphate mannose</span> 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.

<span class="mw-page-title-main">2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase</span> Class of enzymes

In enzymology, a 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase is an enzyme that catalyzes the chemical reaction:

Choline-phosphate cytidylyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a D-ribitol-5-phosphate cytidylyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, an ethanolamine-phosphate cytidylyltransferase is an enzyme that catalyzes the chemical reaction

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

<span class="mw-page-title-main">Glucose-1-phosphate thymidylyltransferase</span>

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

In enzymology, a glycerol-3-phosphate cytidylyltransferase is an enzyme that catalyzes the chemical reaction

Phosphatidate cytidylyltransferase (CDS) is the enzyme that catalyzes the synthesis of CDP-diacylglycerol from cytidine triphosphate and phosphatidate.

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

Thymidine diphosphate glucose is a nucleotide-linked sugar consisting of deoxythymidine diphosphate linked to glucose. It is the starting compound for the syntheses of many deoxysugars.

References

  1. ↑ 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.
  2. ↑ Xue M. He and 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.
  3. 1 2 3 Koropatkin, Nicole M.; Cleland, W. Wallace; Holden, Hazel M. (March 2005). "Kinetic and Structural Analysis of α-d-Glucose-1-phosphate Cytidylyltransferase from Salmonella typhi". Journal of Biological Chemistry. 280 (11): 10774–10780. doi: 10.1074/jbc.m414111200 . ISSN   0021-9258.
  4. ↑ Alonso, Miriam D.; Lagzdins, Erik J.; Lomako, Joseph; Lomako, Wieslawa M.; Whelan, William J. (1995-02-13). "New and specific nucleoside diphosphate glucose substrates for glycogenin". FEBS Letters. 359 (2–3): 110–112. Bibcode:1995FEBSL.359..110A. doi:10.1016/0014-5793(95)00018-5. ISSN   0014-5793.
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