Uridine diphosphate-N-acetylglucosamine

Base Information

• Chemical Name: Uridine diphosphate-N-acetylglucosamine
• CAS No.: 528-04-1
• Molecular Formula: C₁₇H₂₇N₃O₁₇P₂
• Molecular Weight: 607.359
• DSSTox Substance ID: DTXSID10912327
• Nikkaji Number: J568.494C
• Wikipedia: Uridine_diphosphate_N-acetylglucosamine
• Metabolomics Workbench ID: 67603
• Mol file: 528-04-1.mol

Synonyms:Acetylglucosamine, UDP;Diphosphate N-Acetylglucosamine, Uridine;Diphospho-N-Acetylglucosamine, Uridine;N-Acetylglucosamine, Uridine Diphosphate;Pyrophosphoacetylglucosamine, Uridine;UDP Acetylglucosamine;UDPGNAc;Uridine Diphosphate N Acetylglucosamine;Uridine Diphosphate N-Acetylglucosamine;Uridine Diphospho N Acetylglucosamine;Uridine Diphospho-N-Acetylglucosamine;Uridine Pyrophosphoacetylglucosamine

Chemical Property of Uridine diphosphate-N-acetylglucosamine

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 1.10±0.50(Predicted)
• Flash Point: °C
• PSA: 325.48000
• Density: 1.86g/cm³
• LogP: -4.25900
• XLogP3: -6.6
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 10
• Exact Mass: 607.08157040
• Heavy Atom Count: 39
• Complexity: 1080

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)CO)O)O

Technology Process of Uridine diphosphate-N-acetylglucosamine

There total 39 articles about Uridine diphosphate-N-acetylglucosamine 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: 97.9%

N-acetylglucosamine-1-phosphate (28446-21-1,16503-17-6,25249-56-3,6866-69-9) + UTP (63-39-8) → uridine 5'-diphospho-N-acetylglucosamine (528-04-1,2616-63-9,7277-98-7,16465-33-1,19014-00-7,26234-54-8,26575-17-7,27963-82-2,29217-44-5,125639-14-7,16426-39-4,28508-02-3,5547-44-4,83332-40-5)

Guidance literature:

With yeast inorganic pyrophosphatase; N-acetylglucosamine-1-phosphate pyrophosphorylase from C_. jejuni NCTC 11168; tris hydrochloride; magnesium chloride; at 37 ℃; for 2h; pH=7.5;

DOI:10.1016/j.bmcl.2013.06.003

Reference yield: 92.0%

N-acetylglucosamine-1-phosphate (28446-21-1,16503-17-6,25249-56-3,6866-69-9) + uridine 5'-triphosphate trisodium salt (1476-50-2,14264-46-1,19817-92-6,36051-69-1,74674-72-9) → uridine 5'-diphospho-N-acetylglucosamine (528-04-1,2616-63-9,7277-98-7,16465-33-1,19014-00-7,26234-54-8,26575-17-7,27963-82-2,29217-44-5,125639-14-7,16426-39-4,28508-02-3,5547-44-4,83332-40-5)

Guidance literature:

With N-acetyl-D-glucosamine; phosphoenolpyruvic acid; ATP; Glc-1,6-dP₁; magnesium chloride; In various solvents; for 20h;

DOI:10.1039/b207480j

Reference yield: 81.0%

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) + UTP (63-39-8) → uridine 5'-diphospho-N-acetylglucosamine (528-04-1,2616-63-9,7277-98-7,16465-33-1,19014-00-7,26234-54-8,26575-17-7,27963-82-2,29217-44-5,125639-14-7,16426-39-4,28508-02-3,5547-44-4,83332-40-5)

Guidance literature:

With inorganic pyrophosphatase cloned from Pasteurella multocida strain P-1059; N-acetylglucosamine-1-phosphate uridylyltransferase cloned from Pasteurella multocida strain P-1059 (ATCC₁₅₇₄₂); N-acetylhexosamine 1-kinase cloned from Bifidobacterium longum ATCC₅₅₈₁₃; ATP; magnesium chloride; In water; at 37 ℃; pH=8; aq. buffer; Enzymatic reaction;

DOI:10.1039/c1cc14034e

upstream raw materials:

N-acetylglucosamine-1-phosphate

uridine 5'-triphosphate trisodium salt

UTP

S-acetyl coenzyme A

Downstream raw materials:

uridine 5'-diphospho-2-acetamido-2-deoxy-α-D-mannopyranoside

UTP

UDP-glucose

N-acetylgalactosamine-1-phosphate

Refernces

• 1、 Chen,Han,Zhai,Wang,Wang,Chen. "Characterization and mutational analysis of two UDP-galactose 4-epimerases in Streptococcus pneumoniae TIGR4". . p. 37 - 44. Retrieved 2018/02/06.
• 2、 Wagstaff, Ben A.,Rejzek, Martin,Pesnot, Thomas,Tedaldi, Lauren M.,Caputi, Lorenzo,O'Neill, Ellis C.,Benini, Stefano,Wagner, Gerd K.,Field, Robert A.. "Enzymatic synthesis of nucleobase-modified UDP-sugars: Scope and limitations". . p. 17 - 25. Retrieved 2015/03/05.