Uridine diphosphate glucuronic acid

Base Information

• Chemical Name: Uridine diphosphate glucuronic acid
• CAS No.: 2616-64-0
• Molecular Formula: C15H22 N2 O18 P2
• Molecular Weight: 580.29
• UNII: 04SZC4MEFQ
• DSSTox Substance ID: DTXSID00903961
• Nikkaji Number: J247.699A
• Wikipedia: Uridine_diphosphate_glucuronic_acid
• Wikidata: Q277638
• Pharos Ligand ID: L4J3N19N3B8J
• Metabolomics Workbench ID: 37509
• ChEMBL ID: CHEMBL228057
• Mol file: 2616-64-0.mol

Synonyms:Acid, UDP Glucuronic;Acid, Uridine Diphosphoglucuronic;Diphosphoglucuronic Acid, Uridine;Glucuronic Acid, UDP;UDP Glucuronic Acid;UDPGA;Uridine Diphosphate Glucuronic Acid;Uridine Diphosphoglucuronic Acid

Chemical Property of Uridine diphosphate glucuronic acid

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 1.10±0.50(Predicted)
• Flash Point: °C
• PSA: 333.68000
• Density: 2.05g/cm³
• LogP: -4.70140
• XLogP3: -6.4
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 9
• Exact Mass: 580.03428585
• Heavy Atom Count: 37
• Complexity: 1040

Purity/Quality:

99% ^*data from raw suppliers

UDP-ALPHA-D-GALACTURONIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OC3C(C(C(C(O3)C(=O)O)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)C(=O)O)O)O)O)O)O
• Description: An intermediate in the phase II reaction that results in the formation of glucuro_x0002_nic acid conjugates of xenobiotics which contain substituents such as hydroxyl, amino, or sulfhydryl groups, forming the O-, N-, and S-glucuronides, respectively. UDPGA is formed by two reactions: (i) the formation of UDPG from UTP and glucose 1-phosphate and (ii) the formation of UDPGA from UDPG. The two reactions are catalyzed by UDPG pyrophosphorylase and UDPG dehydrogenase, respectively, whereas glucuronide formation is catalyzed by glucuronosyltransferase. Glucuronide formation from xenobiotics is common in all animal groups except insects.

Technology Process of Uridine diphosphate glucuronic acid

There total 37 articles about Uridine diphosphate glucuronic acid 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: 100.0%

UDP (58-98-0) + Sucrose (57-50-1) → UDP-glucuronic acid (2616-64-0)

Guidance literature:

With histidine_-6-nicotinamide adenine dinucleotide hydride oxidase; histidine_-6-uridine 5’-diphosphate-α-D-glucose-dehydrogenase; sucrose synthase 1; NAD; In aq. buffer; at 30 ℃; for 5h; pH=7.8; Enzymatic reaction;

DOI:10.1002/adsc.201500180

Reference yield: 89.0%

D-glucuronic acid (70021-34-0) + UTP (63-39-8) → UDP-glucuronic acid (2616-64-0)

Guidance literature:

With glucuronokinase from Arabidopsis thaliana; pyrophosphatase from E_. coli; UDP-sugar pyrophosphorylasegene from Arabidopsis thaliana; ATP; magnesium chloride; In aq. buffer; at 37 ℃; pH=8; Enzymatic reaction;

DOI:10.1016/j.carres.2015.04.001

Reference yield: 87.0%

UDP-glucose (133-89-1) → UDP-glucuronic acid (2616-64-0)

Guidance literature:

With Tris buffer; NAD; 2-oxo-propionic acid; for 12h; lactate dehydrogenase, uridine 5'-diphosphoglucose dehydrogenase (UDP-Glc dehydrogenase);

DOI:10.1021/jo00019a026

upstream raw materials:

O^5'-(amino-hydroxy-phosphoryl)-uridine

α-D-glucopyranuronic acid 1-phosphate

UDP-glucose

uridine diphospho-α-D-gluco-hexodialdose

Downstream raw materials:

3α-(1''β-D-Glucopyranosiduronyl)-8α-isovaleryloxy-scirpen-3,4β,15-triol 15-acetate

Eugenol glucuronide

Epiandrosterone

androstanedione

Refernces

• 1、 Egger, Sigrid,Chaikuad, Apirat,Klimacek, Mario,Kavanagh, Kathryn L.,Oppermann, Udo,Nidetzky, Bernd. "Structural and kinetic evidence that catalytic reaction of human UPD-glucose 6-dehydrogenase involves covalent thiohemiacetal and thioester enzyme intermediates". . p. 2119 - 2129. Retrieved 2012.
• 2、 Smith et al.. "-". . p. 211. Retrieved 1958.
• 3、 CASTELLANI,DE BERNARD,ZAMBOTTI. "Glucuronic acid formation in epiphyseal cartilage homogenate.". . p. 859 - 859. Retrieved 1957.
• 4、 Campbell,Tanner. "Uridine diphospho-α-D-gluco-hexodialdose: Synthesis and kinetic competence in the reaction catalyzed by UDP-glucose dehydrogenase". . p. 1520 - 1522. Retrieved 1997.
• 5、 Li, Shuang,Wang, Shuaishuai,Wang, Yaqian,Qu, Jingyao,Liu, Xian-Wei,Wang, Peng George,Fang, Junqiang. "Gram-scale production of sugar nucleotides and their derivatives". supporting information. p. 2628 - 2633. Retrieved 2021/04/21.
• 6、 Heinzler, Raphael,Fisch?der, Thomas,Elling, Lothar,Franzreb, Matthias. "Toward Automated Enzymatic Glycan Synthesis in a Compartmented Flow Microreactor System". supporting information. p. 4506 - 4516. Retrieved 2019/08/20.