Uridine 5'-diphospho-N-acetylglucosamine sodium salt

Base Information

• Chemical Name: Uridine 5'-diphospho-N-acetylglucosamine sodium salt
• CAS No.: 91183-98-1
• Molecular Formula: C17H27 N3 O17 P2 . 2 Na
• Molecular Weight: 651.322
• Hs Code.: 29349990
• European Community (EC) Number: 293-820-5
• DSSTox Substance ID: DTXSID401036036
• Mol file: 91183-98-1.mol

Synonyms:91183-98-1;UDP-N-acetyl-D-glucosamine disodium salt;Uridine 5'-diphospho-N-acetylglucosamine sodium salt;Uridine 5'-diphospho-N-acetylglucosamine disodium salt;UDP-GlcNAc Disodium Salt;UDP-|A-D-N-Acetylglucosamine Disodium Salt;disodium;[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-oxidophosphoryl] phosphate;UDPAG;MFCD00799985;DTXSID401036036;AKOS037646463;AS-68944;UDP-a-D-N-Acetylglucosamine Disodium Salt;NS00074322;E85185;Uridine 5'-diphospho-N-acetylglucosamine sodium salt, >=98%;Uridine 5 inverted exclamation mark -Diphospho-N-acetylglucosamine Disodium Salt;Uridine 5 inverted exclamation marka-diphospho-N-acetylglucosamineUDP-a-D-N-Acetylglucosamine Disodium Salt;Uridine 5'-(trihydrogendiphosphate),p'-[2-(acetylamino)-2-Deoxy-a-d-glucopyranosyl]ester,sodium salt(1:2)

Chemical Property of Uridine 5'-diphospho-N-acetylglucosamine sodium salt

Chemical Property:

• Appearance/Colour: WHITE POWDER
• PSA: 331.14000
• LogP: -3.38260
• Storage Temp.: −20°C
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 10
• Exact Mass: 651.04545890
• Heavy Atom Count: 41
• Complexity: 1060

Purity/Quality:

98%,99%, ^*data from raw suppliers

UDP-N-acetyl-D-glucosamine disodium salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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.[Na+].[Na+]
• 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.[Na+].[Na+]
• Uses: Uridine-5'-diphospho-N-acetylglucosamine sodium salt is used as a chemical reagent in studies relating to the synthesis of immunogens. GlcNAc transferase substrate Uridine 5′-diphospho-N-acetylglucosamine (UDP-GlcNAc) sodium salt has been used: as a component of reaction cocktail in endoplasmic reticulum to Golgi transport assay as a reference standard for the quantification of UDP-GlcNAc in liver tissues using high-performance liquid chromatography (HPLC) in testing the glycosylation activity of O-GlcNAc transferase (OGT) against peptide substrate

Technology Process of Uridine 5'-diphospho-N-acetylglucosamine sodium salt

There total 9 articles about Uridine 5'-diphospho-N-acetylglucosamine sodium salt 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: 85.0%

C8H14NO9P(2-)*2Na(1+) + UTP (63-39-8) → P'-[2-(acetylamino)-2-deoxy-α-D-glucopyranosyl] ester uridine 5'-(trihydrogen diphosphate), disodium salt (91183-98-1)

Guidance literature:

With 1,4-dithio-D,L-threitol; magnesium chloride; at 30 ℃; for 3h; pH=7; aq. buffer; Enzymatic reaction;

DOI:10.1021/jo202322k

Reference yield:

C16H36N(1+)*C23H32N3O20P2(1-) → P'-[2-(acetylamino)-2-deoxy-α-D-glucopyranosyl] ester uridine 5'-(trihydrogen diphosphate), disodium salt (91183-98-1)

Guidance literature:

C₁₆H₃₆N⁽¹⁺⁾*C₂₃H₃₂N₃O₂₀P₂^(1-); With ammonium hydroxide; In acetonitrile; for 12h;

DOI:10.1021/jo802021t

Reference yield:

2-azido-2-deoxy-D-glucopyranose-3,4,6-triacetate-1-(dihydrogen phosphate) (1355005-35-4) → P'-[2-(acetylamino)-2-deoxy-α-D-glucopyranosyl] ester uridine 5'-(trihydrogen diphosphate), disodium salt (91183-98-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium methylate / methanol / 1 h / 0 °C

2.1: hydrogen / methanol; water / 20 °C

3.1: methanol; water / 20 °C

3.2: 20 °C

4.1: 1,4-dithio-D,L-threitol; magnesium chloride / 3 h / 30 °C / pH 7 / aq. buffer; Enzymatic reaction

With 1,4-dithio-D,L-threitol; hydrogen; sodium methylate; magnesium chloride; In methanol; water; 1.1: Zemplen deacetylation;

DOI:10.1021/jo202322k

upstream raw materials:

uridine 5'-triphosphate trisodium salt

2-azido-2-deoxy-D-glucopyranose-3,4,6-triacetate-1-(dihydrogen phosphate)

(+)-D-glucosamine hydrochloride

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

Downstream raw materials:

UDP

N-acetylglucosaminylribostamycin

2-N-(benzyloxycarbonyl)-aminoethyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2->3)-[2-acetamido-2-deoxy-O-β-D-galactopyranosyl-(1->4)]-O-(β-D-galactopyranosyl)-(1->4)-O-β-D-glucopyranoside

Refernces

• 1、 Gold, Henrik,Van Delft, Pieter,Meeuwenoord, Nico,Codee, Jeroen D. C.,Filippov, Dmitri V.,Eggink, Gerrit,Overkleeft, Herman S.,Van Der Marel, Gijs A.. "Synthesis of sugar nucleotides by application of phosphoramidites". supporting information; experimental part. p. 9458 - 9460. Retrieved 2009/04/06.