Uridine-5'-diphosphate-glucose

Base Information

• Chemical Name: Uridine-5'-diphosphate-glucose
• CAS No.: 133-89-1
• Molecular Formula: C15H24N2O17P2
• Molecular Weight: 566.306
• European Community (EC) Number: 205-121-4
• UNII: V50K1D7P4Y
• DSSTox Substance ID: DTXSID00157902
• Nikkaji Number: J9.610E
• Wikipedia: Uridine_diphosphate_glucose
• Wikidata: Q424649
• Pharos Ligand ID: BGN6JVYR4JV6
• ChEMBL ID: CHEMBL375951
• Mol file: 133-89-1.mol

Synonyms:Diphosphate Glucose, Uridine;Diphosphoglucose, Uridine;Glucose, UDP;Glucose, Uridine Diphosphate;UDP Glucose;UDPG;Uridine Diphosphate Glucose;Uridine Diphosphoglucose

Chemical Property of Uridine-5'-diphosphate-glucose

Chemical Property:

• PKA: 1.10±0.50(Predicted)
• PSA: 327.61000
• Density: 1.97 g/cm³
• LogP: -5.40690
• XLogP3: -6.3
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 9
• Exact Mass: 566.05502130
• Heavy Atom Count: 36
• Complexity: 964

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OC3C(C(C(C(O3)CO)O)O)O)O)O
• Isomeric SMILES: C1=CN(C(=O)NC1=O)[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
• Description: An intermediate in the phase II reaction that results in the formation of glucose conjugates of xenobiotics which contain substituents such as hydroxyl, amino or sulfhydryl groups, the O-, N-, and S-glucosides, respectively. UDPG is formed from uridine triphosphate and glucose-1- phosphate in a reaction catalyzed by the enzyme UDPG pyro_x0002_phosphorylase. Glucoside formation is common in insects and plants, whereas animals other than insects utilize uridine diphosphate glucuronic acid to form glucuronides.

Technology Process of Uridine-5'-diphosphate-glucose

There total 62 articles about Uridine-5'-diphosphate-glucose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

UTP (63-39-8) + α-D-glucopyranosyl-1-phosphate (59-56-3,27251-84-9,63779-58-8,262856-84-8) → UDP-glucose (133-89-1)

Guidance literature:

With Pasteurella multocida inorganic pyrophosphatase; Bifidobacterium longumuridine 5'-diphosphate-sugarpyrophosphorylase; adenosine-5'-triphosphate; magnesium chloride; In aq. buffer; at 37 ℃; for 2h; pH=8; Enzymatic reaction;

Reference yield: 21.0%

disodium uridine-5'-monophosphate (3387-36-8) + Sucrose (57-50-1) → UDP-glucose (133-89-1)

Guidance literature:

With bovine serum albumine; phospho(enol)pyruvate CHA-salt; tris hydrochloride; uridine 5'-triphosphate trisodium salt; magnesium chloride; diothiothreitol; at 30 ℃; for 21h; sucrose synthase, pyruvate kinase, nucleoside monophosphate kinase;

DOI:10.1016/0040-4020(95)01081-5

Reference yield:

α-D-Glucopyranoside 1-(disodium phosphate) (56401-20-8) + uridine 5'-triphosphate sodium salt (19817-92-6) → UDP-glucose (133-89-1)

Guidance literature:

With inorganic pyrophosphatase; uridine-5'-diphosphoglucose pyrophosphorylase; enzymatically at pH 7.6;

DOI:10.1021/jo00293a030

upstream raw materials:

α-D-Glucopyranoside 1-(disodium phosphate)

uridine 5'-triphosphate sodium salt

α-D-glucose 6-phosphate

UTP

Downstream raw materials:

1‐O‐sinapoyl‐beta‐D‐glucose

Ac-Tyr-Asp-Phe-Leu-Pro-Glu-Thr(Galβ(1,4)GlcNAc(β1,6)GalNAcα)-Glu-NH2

Ac-Tyr(OSO3^-)-Asp-Phe-Leu-Pro-Glu-Thr(Galβ(1,4)GlcNAc(β1,6)GalNAcα)-Glu-NH2

lacto-N-neo-tetraose

Refernces

• 1、 Smith,Mills. "-". . p. 152. Retrieved 1955.
• 2、 Li, Li-Na,Kong, Jian-Qiang. "Transcriptome-wide identification of sucrose synthase genes in Ornithogalum caudatum". . p. 18778 - 18792. Retrieved 2016.
• 3、 MILLS,ONDARZA,SMITH. "The uridyl transferase of liver.". . p. 159 - 160. Retrieved 1954.
• 4、 Kurahashi, Kiyoshi. "Enzyme formation in galactose-negative mutants of Escherichia coli". . p. 114 - 116. Retrieved 1957.
• 5、 Fang, Junqiang,Xue, Mengyang,Gu, Guofeng,Liu, Xian-Wei,Wang, Peng George. "A chemoenzymatic route to synthesize unnatural sugar nucleotides using a novel N-acetylglucosamine-1-phosphate pyrophosphorylase from Camphylobacter jejuni NCTC 11168". . p. 4303 - 4307. Retrieved 2013.
• 6、 Fang, Junqiang,Guan, Wanyi,Cai, Li,Gu, Guofeng,Liu, Xianwei,Wang, Peng George. "Systematic study on the broad nucleotide triphosphate specificity of the pyrophosphorylase domain of the N-acetylglucosamine-1-phosphate uridyltransferase from Escherichia coli K12". . p. 6429 - 6432. Retrieved 2009.
• 7、 Yang, Ting,Echols, Merritt,Martin, Andy,Bar-Peled, Maor. "Identification and characterization of a strict and a promiscuous N-acetylglucosamine-1-P uridylyltransferase in Arabidopsis". . p. 275 - 284. Retrieved 2010.
• 8、 Zhou, Guangyan,Liu, Xianwei,Su, Doris,Li, Lei,Xiao, Min,Wang, Peng G.. "Large scale enzymatic synthesis of oligosaccharides and a novel purification process". . p. 311 - 314. Retrieved 2011.
• 9、 Ryu, Soo-In,Kim, Jeong-Eun,Kim, Eun-Joo,Chung, Seung-Kyung,Lee, Soo-Bok. "Catalytic reversibility of Pyrococcus horikoshii trehalose synthase: Efficient synthesis of several nucleoside diphosphate glucoses with enzyme recycling". . p. 128 - 134. Retrieved 2011.
• 10、 Miyagawa, Atsushi,Toyama, Sanami,Ohmura, Ippei,Miyazaki, Shun,Kamiya, Takeru,Yamamura, Hatsuo. "One-Step Synthesis of Sugar Nucleotides". . p. 15645 - 15651. Retrieved 2020.