Uridine 5'-diphosphoric acid beta-(alpha-D-fucopyranosyl) ester

Base Information

• Chemical Name: Uridine 5'-diphosphoric acid beta-(alpha-D-fucopyranosyl) ester
• CAS No.: 16375-63-6
• Molecular Formula: C₁₅H₂₄N₂O₁₆P₂
• Molecular Weight: 550.307
• DSSTox Substance ID: DTXSID701139683
• Nikkaji Number: J1.270.522K
• ChEMBL ID: CHEMBL595940
• Mol file: 16375-63-6.mol

Synonyms:CHEMBL595940;DTXSID701139683;BDBM50304031;Uridine 5'-diphosphoric acid beta-(alpha-D-fucopyranosyl) ester;Diphosphoric Acid 1''''-alpha-D-[1'''']Fucopyranosyl Ester 2-(uridine-5''-yl)ester;Uridine 5'-(trihydrogen diphosphate), P'-(6-deoxy-alpha-D-galactopyranosyl) ester;16375-63-6

Chemical Property of Uridine 5'-diphosphoric acid beta-(alpha-D-fucopyranosyl) ester

Chemical Property:

• XLogP3: -6.1
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 8
• Exact Mass: 550.06010668
• Heavy Atom Count: 35
• Complexity: 948

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)O)O)O
• Isomeric SMILES: C[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)O)O)O

Technology Process of Uridine 5'-diphosphoric acid beta-(alpha-D-fucopyranosyl) ester

There total 14 articles about Uridine 5'-diphosphoric acid beta-(alpha-D-fucopyranosyl) ester 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: 68.0%

D-Fucose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) + uridine 5'-triphosphate trisodium salt (1476-50-2,14264-46-1,19817-92-6,36051-69-1,74674-72-9) → UDP-6-deoxy-Gal (16375-63-6,30174-43-7)

Guidance literature:

With pyrophosphatase, inorganic from yeast; UTP-glucose-1-phosphate galactokinase from Streptococcus pneumoniae TIGR₄; UTP-glucose-1-phosphate uridylyltransferase from Streptococcus pneumoniae TIGR₄; adenosine 5'-triphosphate sodium salt; magnesium chloride; In aq. buffer; at 42 ℃; for 24h; pH=8; Enzymatic reaction;

DOI:10.1016/j.carres.2013.03.005

Reference yield: 16.0%

bis(triethylammonium)-α-D-fucopyranosyl phosphate + 4-morpholine-N,N'-dicyclohexyl-carboxamidine uridine-5'-monophosphate → UDP-6-deoxy-Gal (16375-63-6,30174-43-7)

Guidance literature:

In dimethyl sulfoxide; at 25 ℃; for 144h;

DOI:10.1006/bioo.1994.1012

Reference yield:

D-Fucose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) + UTP (63-39-8) → UDP-6-deoxy-Gal (16375-63-6,30174-43-7)

Guidance literature:

With pyrophosphatase; Streptococcus pneumoniae TIGR₄ galactokinase; Arabidopsis thaliana uridine-diphosphate-sugar pyrophosphorylase; ATP; magnesium chloride; In aq. buffer; at 42 ℃; for 1h; pH=8; Enzymatic reaction;

DOI:10.1016/j.bmcl.2013.04.090

upstream raw materials:

2,3,4-tri-O-acetyl-6-deoxy-D-galactopyranose

2,3,4-tri-O-acetyl-6-deoxy-α-D-galactopyranosyl 1-phosphate dibenzyl ester

2,3,4-tri-O-acetyl-D-fucopyranosyl bromide

D-Fucose

Refernces

• 1、 Zou, Yang,Xue, Mengyang,Wang, Wenjun,Cai, Li,Chen, Leilei,Liu, Jun,Wang, Peng George,Shen, Jie,Chen, Min. "One-pot three-enzyme synthesis of UDP-Glc, UDP-Gal, and their derivatives". supporting information. p. 76 - 81. Retrieved 2013/06/27.
• 2、 Kajihara,Endo,Ogasawara,Kodama,Hashimoto. "Enzymic transfer of 6-modified D-galactosyl residues: Synthesis of biantennary penta- and hepta-saccharides having two 6-deoxy-D-galactose residues at the nonreducing end and evaluation of 6-deoxy-D-galactosyl transfer to glycoprotein using bovine β-(1 4)-galactosyltransferase and UDP-6-deoxy-D-galactose". . p. 273 - 294. Retrieved 2007/10/02.