[(2R,3R,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-[hydroxy-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-phosphoryl]oxy-phosphinic acid

Base Information

• Chemical Name: [(2R,3R,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-[hydroxy-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-phosphoryl]oxy-phosphinic acid
• CAS No.: 5750-57-2
• Molecular Formula: C16H25 N5 O16 P2
• Molecular Weight: 605.346
• Mol file: 5750-57-2.mol

Synonyms:Guanosine5'-(trihydrogen pyrophosphate), mono-a-D-glucopyranosyl ester (8CI); Guanosine5'-pyrophosphate, a-D-glucopyranosyl ester (6CI,7CI); GDP-D-glucose; GDP-glucose; GDP-a-D-glucose; GDPG; Guanosine5'-(trihydrogen diphosphate), P'-D-glucopyranosyl ester; Guanosine5'-(trihydrogen pyrophosphate), mono-D-glucopyranosyl ester; Guanosine 5'-(trihydrogenpyrophosphate), mono-D-glucosyl ester; Guanosine 5'-(trihydrogenpyrophosphate), monoglucopyranosyl ester; Guanosine 5'-diphosphate glucose;Guanosine 5'-diphosphate-D-glucose; Guanosine 5'-pyrophosphate, D-glucosylester; Guanosine 5'-pyrophosphate, glucosyl ester; Guanosine 5'-pyrophosphate, a-D-glucosyl ester; Guanosinediphosphate D-glucose; Guanosine diphosphate glucose; Guanosinediphosphoglucose; Guanosine pyrophosphates, a-D-glucopyranosyl ester

Chemical Property of [(2R,3R,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-[hydroxy-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-phosphoryl]oxy-phosphinic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1062.9°Cat760mmHg
• Flash Point: 596.6°C
• PSA: 380.80000
• Density: 2.51g/cm³
• LogP: -4.79570

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [(2R,3R,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-[hydroxy-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-phosphoryl]oxy-phosphinic acid

There total 22 articles about [(2R,3R,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-[hydroxy-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-phosphoryl]oxy-phosphinic 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: 94.0%

D-Mannose (530-26-7) + Guanosine 5'-triphosphate (86-01-1,72490-81-4) → guanosine-5'-diphosphate (146-91-8) + guanosine 5'-diphospho-D-mannose (991-43-5,3123-67-9,5572-04-3,5750-57-2,6815-91-4,10108-97-1,20236-92-4,20406-59-1,26234-84-4,26378-86-9,41432-88-6,55331-69-6,78391-95-4)

Guidance literature:

With guanosine 50-diphosphate (GDP)-mannose pyrophosphorylasefrom Pyrococcus furiosus; N-acetylhexosamine 1-kinase from Bifidobacterium infantis; magnesium chloride; Escherichia coli inorganic pyrophosphatase; In aq. buffer; at 37 ℃; for 24h; pH=8; Enzymatic reaction;

DOI:10.1021/ol402585c

Reference yield: 72.0%

D-Glucose (2280-44-6) + Guanosine 5'-triphosphate (86-01-1,72490-81-4) → guanosine-5'-diphosphate (146-91-8) + guanosine-5’-diphospho-α-D-glucopyranosyl (5750-57-2)

Guidance literature:

With guanosine 50-diphosphate (GDP)-mannose pyrophosphorylasefrom Pyrococcus furiosus; N-acetylhexosamine 1-kinase from Bifidobacterium infantis; magnesium chloride; Escherichia coli inorganic pyrophosphatase; In aq. buffer; at 37 ℃; for 24h; pH=8; Enzymatic reaction;

DOI:10.1021/ol402585c

Reference yield: 54.0%

α-mannose 1-phosphate dicyclohexylammonium salt (50615-45-7,50820-78-5,72946-45-3,77895-07-9) + Guanosine 5'-triphosphate (36051-31-7) → guanosine 5'-diphospho-D-mannose (991-43-5,3123-67-9,5572-04-3,5750-57-2,6815-91-4,10108-97-1,20236-92-4,20406-59-1,26234-84-4,26378-86-9,41432-88-6,55331-69-6,78391-95-4)

Guidance literature:

With ethylenediaminetetraacetic acid; GDP-mannose pyrophosphorylase; sodium fluoride; magnesium chloride; for 24h; Ambient temperature; pH 7.5;

DOI:10.1021/jo00293a030

upstream raw materials:

D-Glucose

Guanosine 5'-triphosphate

mannose-1-phosphate

α-mannose 1-phosphate dicyclohexylammonium salt

Downstream raw materials:

guanosine-5'-diphospho-β-L-fucose

GDP-L-gulose

guanosine 5'-diphospho-β-L-galactopyranoside

[5''-2H]-GDP-6-deoxy-4-keto-D-mannose

Refernces

• 1、 Chen, Zonggang,Gu, Guofeng,Jin, Guoxia,Li, Siqiang,Wang, Hong. "Exploring the broad nucleotide triphosphate and sugar-1-phosphate specificity of thymidylyltransferase Cps23FL from: Streptococcus pneumonia serotype 23F". . p. 30110 - 30114. Retrieved 2020/09/07.
• 2、 Li, Lei,Liu, Yonghui,Wan, Yue,Li, Yanhong,Chen, Xi,Zhao, Wei,Wang, Peng George. "Efficient enzymatic synthesis of guanosine 5′-diphosphate-sugars and derivatives". supporting information. p. 5528 - 5530. Retrieved 2013/11/19.