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
• General Description: Uridine 5'-(trihydrogen diphosphate), mono-alpha-d-glucopyranosyl ester (UDP-glucose) is a key nucleotide sugar involved in glycosylation processes, serving as a glucose donor in the biosynthesis of glycoproteins and other glycoconjugates. The study highlights its analogues as potential inhibitors of protein glycosylation, demonstrating antiviral activity against HSV-1. Structural modifications, such as specific protecting groups on the glucose moiety, were found to enhance inhibitory effects, underscoring Uridine 5'-(trihydrogen diphosphate), mono-alpha-d-glucopyranosyl ester's relevance in therapeutic development for viral infections.

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:

Galα(1->3)Galβ(1->4)GlcNAc

1‐O‐sinapoyl‐beta‐D‐glucose

uridine 5'-(2-amino-2-deoxy-α-D-galactopyranosyl diphosphate)

(2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6S)-6-((2R,3S,4R,5R)-6-Benzyloxy-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Refernces

Uridine 5'-diphosphate glucose analogues. Inhibitors of protein glycosylation that show antiviral activity

10.1021/jm00379a010

The research aimed to synthesize and evaluate a series of uridine 5’-diphosphate glucose analogues as inhibitors of protein glycosylation, with the goal of demonstrating their antiviral activity. The study focused on the synthesis of these analogues by reacting various protected glucose derivatives with chlorosulfonyl isocyanate and 2’,3’-O-isopropylideneuridine. The synthesized compounds were then tested for their ability to inhibit protein glycosylation in herpes simplex virus type 1 (HSV-1) infected cells and for their antiviral effects. The results showed that certain analogues, particularly compound 13, effectively inhibited protein glycosylation and exhibited significant antiviral activity against HSV-1, suggesting their potential as therapeutic agents. The study concluded that the presence of specific protecting groups on the glucose moiety influenced the antiviral efficacy, highlighting the importance of structural features in the design of effective glycosylation inhibitors.