(2s,3s,4r,5r,6r)-5-Acetamido-6-[[[(2r,3s,4r,5r)-5-(2,4-Dioxopyrimidin-1-Yl)-3,4-Dihydroxy-Oxolan-2-Yl]methoxy-Hydroxy-Phosphoryl]oxy-Hydroxy-Phosphoryl]oxy-3,4-Dihydroxy-Oxane-2-Carboxylic Acid

Base Information

• Chemical Name: (2s,3s,4r,5r,6r)-5-Acetamido-6-[[[(2r,3s,4r,5r)-5-(2,4-Dioxopyrimidin-1-Yl)-3,4-Dihydroxy-Oxolan-2-Yl]methoxy-Hydroxy-Phosphoryl]oxy-Hydroxy-Phosphoryl]oxy-3,4-Dihydroxy-Oxane-2-Carboxylic Acid
• CAS No.: 24758-79-0
• Molecular Formula: C₁₇H₂₅N₃O₁₈P₂
• Molecular Weight: 621.342
• DSSTox Substance ID: DTXSID701110984
• Metabolomics Workbench ID: 63642
• Nikkaji Number: J2.436.806H
• Mol file: 24758-79-0.mol

Synonyms:UDP-N-acetyl-D-glucosaminuronate;(2s,3s,4r,5r,6r)-5-Acetamido-6-[[[(2r,3s,4r,5r)-5-(2,4-Dioxopyrimidin-1-Yl)-3,4-Dihydroxy-Oxolan-2-Yl]methoxy-Hydroxy-Phosphoryl]oxy-Hydroxy-Phosphoryl]oxy-3,4-Dihydroxy-Oxane-2-Carboxylic Acid;UDP-2-acetamido-2-deoxy-alpha-D-glucuronic acid;uridine 5-{3-[2-(acetylamino)-2-deoxy-alpha-D-glucopyranosyluronic acid] dihydrogen diphosphate};UDP-N-acetyl-2-amino-2-deoxy-alpha-D-glucuronate;HP7;CHEBI:65047;DTXSID701110984;24758-79-0;C04573;(2S,3S,4R,5R,6R)-5-(acetylamino)-6-{[(R)-{[(S)-{[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]oxy}-3,4-dihydroxytetrahydro-2H-pyran-2-carboxylic acid (non-preferred name);(2S,3S,4R,5R,6R)-5-acetamido-6-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-3,4-dihydroxyoxane-2-carboxylic acid

Chemical Property of (2s,3s,4r,5r,6r)-5-Acetamido-6-[[[(2r,3s,4r,5r)-5-(2,4-Dioxopyrimidin-1-Yl)-3,4-Dihydroxy-Oxolan-2-Yl]methoxy-Hydroxy-Phosphoryl]oxy-Hydroxy-Phosphoryl]oxy-3,4-Dihydroxy-Oxane-2-Carboxylic Acid

Chemical Property:

• XLogP3: -6.4
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 10
• Exact Mass: 621.06083495
• Heavy Atom Count: 40
• Complexity: 1150

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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)C(=O)O)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)C(=O)O)O)O

Technology Process of (2s,3s,4r,5r,6r)-5-Acetamido-6-[[[(2r,3s,4r,5r)-5-(2,4-Dioxopyrimidin-1-Yl)-3,4-Dihydroxy-Oxolan-2-Yl]methoxy-Hydroxy-Phosphoryl]oxy-Hydroxy-Phosphoryl]oxy-3,4-Dihydroxy-Oxane-2-Carboxylic Acid

There total 1 articles about (2s,3s,4r,5r,6r)-5-Acetamido-6-[[[(2r,3s,4r,5r)-5-(2,4-Dioxopyrimidin-1-Yl)-3,4-Dihydroxy-Oxolan-2-Yl]methoxy-Hydroxy-Phosphoryl]oxy-Hydroxy-Phosphoryl]oxy-3,4-Dihydroxy-Oxane-2-Carboxylic 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:

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) → UDP-N-acetyl-D-glucosaminuronic acid (24758-79-0,21654-37-5,25174-34-9)

Guidance literature:

With oxygen; platinum;

DOI:10.1039/b313316h

Reference yield:

UDP-N-acetyl-D-glucosaminuronic acid (24758-79-0,21654-37-5,25174-34-9) → UDP-GlcNAc3NAcA (112529-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Bordetella petrii WlbC; Thermus thermophilus WlbA; Glutamic acid / 12 h / 30 °C / pH 8 / aq. buffer; Enzymatic reaction

2: Bordetella petrii WlbB N-acetyltransferase; 5,5'-dithiobis-(2-nitrobenzoic acid) / 25 °C / pH 7.5 / aq. buffer; Enzymatic reaction

With Glutamic acid; 5,5'-dithiobis-(2-nitrobenzoic acid); Bordetella petrii WlbB N-acetyltransferase; Bordetella petrii WlbC; Thermus thermophilus WlbA;

DOI:10.1021/bi1005738

upstream raw materials:

uridine 5'-diphospho-N-acetylglucosamine

Downstream raw materials:

UDP-GlcNAc3NAcA