(2S,3S,4S,5R,6S)-5-{[{[{[(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}-3,4,6-trihydroxytetrahydro-2H-pyran-2-carboxylic acid (non-preferred name)

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-5-{[{[{[(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}-3,4,6-trihydroxytetrahydro-2H-pyran-2-carboxylic acid (non-preferred name)
• CAS No.: 106864-00-0
• Molecular Formula: C₁₅H₂₂N₂O₁₈P₂
• Molecular Weight: 580.29
• Mol file: 106864-00-0.mol

Synonyms:

Chemical Property of (2S,3S,4S,5R,6S)-5-{[{[{[(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}-3,4,6-trihydroxytetrahydro-2H-pyran-2-carboxylic acid (non-preferred name)

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 2.05g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R,6S)-5-{[{[{[(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}-3,4,6-trihydroxytetrahydro-2H-pyran-2-carboxylic acid (non-preferred name)

There total 11 articles about (2S,3S,4S,5R,6S)-5-{[{[{[(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}-3,4,6-trihydroxytetrahydro-2H-pyran-2-carboxylic acid (non-preferred name) 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: 70.0%

D-galacturonic acid (6294-16-2) + UTP (63-39-8) → Uridine pyrophosphate galacturonic acid (2616-64-0,7305-43-3,50722-58-2,106864-00-0,14520-48-0,30329-32-9,3545-73-1,5918-40-1)

Guidance literature:

With galactokinase from Bifidobacterium infantis ATCC₁₅₆₉₇; pyrophosphatase from E_. coli; UDP-sugar pyrophosphorylasegene from Arabidopsis thaliana; ATP; magnesium chloride; In aq. buffer; at 37 ℃; pH=8; Enzymatic reaction;

DOI:10.1016/j.carres.2015.04.001

Reference yield: 39.0%

D-galacturonic acid (489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7) + UTP (63-39-8) → Uridine pyrophosphate galacturonic acid (2616-64-0,7305-43-3,50722-58-2,106864-00-0,14520-48-0,30329-32-9,3545-73-1,5918-40-1)

Guidance literature:

With recombinant Arabidopsis thaliana UDP-sugar pyrophosphorylase; recombinant Bifidobacterium infantis galactokinase; recombinant Pasteurella multocida inorganic pyrophosphatase; ATP; magnesium chloride; In aq. buffer; at 37 ℃; for 30h; pH=7; chemoselective reaction; Catalytic behavior; Enzymatic reaction;

DOI:10.1039/c4cc10306h

Reference yield:

→ uridine diphosphoglucuronic acid (2616-64-0,7305-43-3,50722-58-2,106864-00-0,14520-48-0,30329-32-9,3545-73-1,5918-40-1)

Guidance literature:

1,3-Dicyclohexyl-guanidiniumsalz v. Uridin-5'-phosphoramidat, Triaethylammoniumsalz v. β-Glucuronsaeure-1-phosphat, in wfr. Py.(37grad);;

upstream raw materials:

UDP-glucose

UTP

UDP-glucuronic acid

α-D-glucopyranosyl-1-phosphate

Downstream raw materials:

zidovudine-glucuronide

Refernces

• 1、 Borg, Annika J. E.,Dennig, Alexander,Weber, Hansj?rg,Nidetzky, Bernd. "Mechanistic characterization of UDP-glucuronic acid 4-epimerase". . p. 1163 - 1178. Retrieved 2021.
• 2、 Guo, Yuxi,Fang, Junqiang,Li, Tiehai,Li, Xu,Ma, Cheng,Wang, Xuan,Wang, Peng G.,Li, Lei. "Comparing substrate specificity of two UDP-sugar pyrophosphorylases and efficient one-pot enzymatic synthesis of UDP-GlcA and UDP-GalA". . p. 1 - 5. Retrieved 2015.
• 3、 Li, Shuang,Wang, Shuaishuai,Wang, Yaqian,Qu, Jingyao,Liu, Xian-Wei,Wang, Peng George,Fang, Junqiang. "Gram-scale production of sugar nucleotides and their derivatives". supporting information. p. 2628 - 2633. Retrieved 2021/04/21.