ウリジン二リン酸グルコース
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Uridine diphosphate glucose
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Names |
IUPAC name
[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
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Other names
UDP-glucose
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Identifiers |
CAS Registry Number
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133-89-1 Y |
ChEBI |
CHEBI:52249 Y |
ChEMBL |
ChEMBL375951 Y |
ChemSpider |
8308 Y |
InChI
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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 Y
Key: HSCJRCZFDFQWRP-JZMIEXBBSA-N Y
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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
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IUPHAR/BPS
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1783 |
Jmol-3D images |
Image |
MeSH |
Uridine+Diphosphate+Glucose |
PubChem |
8629 |
SMILES
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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
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Properties |
Chemical formula
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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).
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Y verify (what is: Y/N?) |
Infobox references |
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Uridine diphosphate glucose (uracil-diphosphate glucose, UDP-glucose) is a nucleotide sugar. It is involved in glycosyltransferase reactions in metabolism.
Contents
- 1 Functions
- 2 Components
- 3 References
- 4 See also
Functions
It is used in nucleotide sugars metabolism as an activated form of glucose as a substrate for enzymes called glucosyltransferases.[1]
It 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, the pentose sugar ribose, glucose, and the nucleobase uracil.
References
- ^ Rademacher T, Parekh R, Dwek R (1988). "Glycobiology". Annu Rev Biochem 57: 785–838. doi:10.1146/annurev.bi.57.070188.004033. PMID 3052290.
See also
- Nucleoside
- Nucleotide
- DNA
- RNA
- Oligonucleotide
- Uracil
- Uridine diphosphate
- TDP-glucose
Types of nucleotide sugars
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- CDP-glucose
- GDP-mannose
- TDP-glucose
- UDP-glucose
- UDP-galactose
- UDP-glucuronic acid
- UDP-N-acetylglucosamine
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Index of biochemical families
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Carbohydrates |
- Alcohols
- Glycoproteins
- Glycosides
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Lipids |
- Eicosanoids
- Fatty acids
- Glycerides
- Phospholipids
- Sphingolipids
- Steroids
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Nucleic acids |
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Proteins |
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Other |
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Fructose and galactose metabolic intermediates
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Fructose |
- Fructose-1-phosphate → DHAP/Glyceraldehyde → Glyceraldehyde 3-phosphate
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Galactose |
- Galactose-1-phosphate → Glucose 1-phosphate → Glucose 6-phosphate → Fructose 6-phosphate
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- Uridine diphosphate galactose
- Uridine diphosphate glucose
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Mannose |
- Mannose-6-phosphate → Fructose 6-phosphate
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Index of inborn errors of metabolism
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Description |
- Metabolism
- Enzymes and pathways: citric acid cycle
- pentose phosphate
- glycoproteins
- glycosaminoglycans
- phospholipid
- cholesterol and steroid
- sphingolipids
- eicosanoids
- amino acid
- urea cycle
- nucleotide
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Disorders |
- Citric acid cycle and electron transport chain
- Glycoprotein
- Proteoglycan
- Fatty-acid
- Phospholipid
- Cholesterol and steroid
- Eicosanoid
- Amino acid
- Purine-pyrimidine
- Heme metabolism
- Symptoms and signs
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Treatment |
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Index of nutrition
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Description |
- Vitamins
- Cofactors
- Metal metabolism
- Fats
- metabolism
- intermediates
- lipoproteins
- Sugars
- Glycolysis
- Glycogenesis and glycogenolysis
- Fructose and galactose
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Disease |
- Vitamins
- Carbohydrate
- Lipid
- Metals
- Other
- Symptoms and signs
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Treatment |
- Drugs
- Vitamins
- Mineral supplements
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English Journal
- Effect of Gemfibrozil, Rifampicin, or Probenecid on the Pharmacokinetics of the SGLT2 Inhibitor Empagliflozin in Healthy Volunteers.
- Macha S1, Koenen R2, Sennewald R2, Schöne K3, Hummel N2, Riedmaier S2, Woerle HJ3, Salsali A3, Broedl UC3.Author information 1Boehringer Ingelheim Pharmaceuticals, Inc, Ridgefield, Connecticut. Electronic address: sreeraj.macha@boehringer-ingelheim.com.2Boehringer Ingelheim Pharma GmbH & Co KG, Biberach, Germany.3Boehringer Ingelheim Pharma GmbH & Co KG, Ingelheim, Germany.AbstractBACKGROUND: Empagliflozin is a potent, oral, selective inhibitor of sodium glucose cotransporter 2 in development for the treatment of type 2 diabetes mellitus.
- Clinical therapeutics.Clin Ther.2014 Jan 31. pii: S0149-2918(14)00011-3. doi: 10.1016/j.clinthera.2014.01.003. [Epub ahead of print]
- BACKGROUND: Empagliflozin is a potent, oral, selective inhibitor of sodium glucose cotransporter 2 in development for the treatment of type 2 diabetes mellitus.OBJECTIVE: The goal of these studies was to investigate potential drug-drug interactions between empagliflozin and gemfibrozil (an organic a
- PMID 24491572
- Effect of uracil on pullulan production by Aureobasidium pullulans CGMCC1234.
- Sheng L, Zhu G, Tong Q.Author information The State Key Laboratory of Food Science and Technology, School of Food Science and Technology, Jiangnan University, Wuxi 214122, China.AbstractEffect of uracil on the pullulan production, biomass and uridine phosphorylase (UPase) activity was studied in this research. Uracil was found to enhance pullulan accumulation and the addition time of uracil was crucial to pullulan production. Pullulan yield of 49.07 g/L was achieved by adding 5mM uracil at 48 h, by comparison to 37.72 g/L obtained with the control. UPase activity could not be detected at early growth stage of Aureobasidium pullulans, but stimulated by added uracil at logarithmic phase and stationary phase. The time course study on the fermentation of pullulan demonstrates that pullulan production was not closely associated with biomass accumulation. Results indicate that the increased pullulan yield brought by uracil was correlated with UPase activity.
- Carbohydrate polymers.Carbohydr Polym.2014 Jan 30;101:435-7. doi: 10.1016/j.carbpol.2013.09.063. Epub 2013 Sep 30.
- Effect of uracil on the pullulan production, biomass and uridine phosphorylase (UPase) activity was studied in this research. Uracil was found to enhance pullulan accumulation and the addition time of uracil was crucial to pullulan production. Pullulan yield of 49.07 g/L was achieved by adding 5mM u
- PMID 24299794
- Identification and characterization of granule bound starch synthase I (GBSSI) gene of tartary buckwheat (Fagopyrum tataricum Gaertn.).
- Wang X1, Feng B1, Xu Z1, Sestili F2, Zhao G1, Xiang C1, Lafiandra D2, Wang T3.Author information 1Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.2Department of Agriculture, Forestry, Nature & Energy, University of Tuscia, Viterbo, Italy.3Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China. Electronic address: wangtao@cib.ac.cn.AbstractTartary buckwheat (Fagopyrum tataricum Gaertn.) is increasingly considered as an important functional food material because of its rich nutraceutical compounds. Reserve starch is the major component of tartary buckwheat seed. However, the gene sequences and the molecular mechanism of tartary buckwheat starch synthesis are unknown so far. In this study, the complete genomic sequence and full-size cDNA coding tartary buckwheat granule-bound starch synthase I (FtGBSSI), which is responsible for amylose synthesis, were isolated and analyzed. The genomic sequence of the FtGBSSI contained 3947 nucleotides and was composed of 14 exons and 13 introns. The cDNA coding sequence of FtGBSSI shared 63.3%-75.1% identities with those of dicots and 56.6%-57.5% identities with monocots (Poaceae). In deduced amino acid sequence of FtGBSSI, eight motifs conserved among plant starch synthases were identified. A cleavage at the site IVC↓G of FtGBSSI protein produces the chloroplast transit sequence of 78 amino acids and the mature protein of 527 amino acids. The FtGBSSI mature protein showed an identity of 73.4%-77.8% with dicot plants, and 67.6%-70.4% with monocot plants (Poaceae). The mature protein was composed of 20 α-helixes and 16 β-strands, and folds into two main domains, N- and C-terminal domains. The critical residues which are involved in ADP and sugar binding were predicted. These results will be useful to modulate starch composition of buckwheat kernels with the aim to produce novel improved varieties in future breeding programs.
- Gene.Gene.2014 Jan 25;534(2):229-35. doi: 10.1016/j.gene.2013.10.053. Epub 2013 Nov 6.
- Tartary buckwheat (Fagopyrum tataricum Gaertn.) is increasingly considered as an important functional food material because of its rich nutraceutical compounds. Reserve starch is the major component of tartary buckwheat seed. However, the gene sequences and the molecular mechanism of tartary buckwhe
- PMID 24211386
Japanese Journal
- マウス腹腔マクロファージにおけるP2Y14受容体の発現と機能
- 工藤 藤美,西口 直樹,伊藤 京子 [他],Nakano Manabu,Ito Koichi
- 弘前醫學 63(2/3/4), 96-104, 2012-00-00
- … The P2Y14 receptor is activated by UDP-glucose (UDPG), which is a well-known glycosyl donor that participates in the biosynthesis of carbohydrates, and is widely expressed in immune cells. … During inflammation and mechanical stress, damaged cells release nucleotides, including ATP and UDPG, as danger signals that act as P2Y receptor agonists. … Consistent with this observation, we revealed that administration of UDPG to mice with induced peritonitis increased the number of CD11blow macrophages. …
- NAID 110009550204
- 84. UDP-glucose非依存性イネ由来糖転移酵素に関わる糖供与体の探索(口頭発表,植物化学調節学会第46回大会)
- 宮澤 吉郎,瀬戸 義哉,小野 祐太朗,佐藤 道大,高橋 公咲,和久田 真司,松井 博和,鍋田 憲助,松浦 英幸
- 植物化学調節学会研究発表記録集 (46), 100, 2011-10-03
- … In order to establish functions of these compounds, we previously purified and characterized a glucosyltransferase in rice, that catalyzes the glucosylation from TA to TAG using UDPG as a glucose donor [1]. … Moreover, we found out the existence of UDPG-independent one in the crude enzyme, that is more specific to TA than that one. … In order to understand this glucosylation, we investigated a glucose donor except UDPG in this study. …
- NAID 110008902493
- Role of Jasmonic Acid in Alteration of Ginsenoside Heterogeneity in Elicited Cell Cultures of Panax notoginseng(PLANT BIOTECHNOLOGY)
- Hu Feng-Xian,Zhong Jian-Jiang
- Journal of bioscience and bioengineering 104(6), 513-516, 2007-12-25
- … In this work, the activities of two enzymes related to ginsenoside heterogeneity (distribution), protopanaxdiol 6-hydroxylase (P6H) and UDPG-ginsenoside Rd glucosyltransferase (UGRdGT), were examined in cell cultures of P. …
- NAID 110006533089
Related Links
- (UDPG-T) activity was 0.14 and 0.22 units in two fetuses aged 17 fresh adult mouse liver (5) is difficult to interpret because of the and 22 weeks, respectively, and less than 0.1 unit in 15 fetuses, lack of comparable data in ...
- UDPG Abbreviation for uridine diphosphoglucose. ... Disclaimer All content on this website, including dictionary, thesaurus, literature, geography, and other reference data is for informational purposes only.
Related Pictures
★リンクテーブル★
[★]
- 英
- uridine diphosphate glucose, UDPG
- 同
- UDPグルコース UDP-グルコース UDP-glucose UDPGlc
- 関
- グリコーゲン
グリコーゲン合成
[★]
- 同
- uridinediphosphoglucuronate glucuronosyltransferase
[★]
- 関
- See Uridine diphosphate glucose
[★]
- 関
- Uridine diphosphate galactose
[★]
- 関
- uridine diphosphate