Guanosine-5'-diphosphate

Base Information

• Chemical Name: Guanosine-5'-diphosphate
• CAS No.: 146-91-8
• Molecular Formula: C10H15N5O11P2
• Molecular Weight: 443.204
• DSSTox Substance ID: DTXSID90163254
• Nikkaji Number: J40.056D
• Wikipedia: Guanosine_diphosphate
• Wikidata: Q422582
• NCI Thesaurus Code: C535
• Pharos Ligand ID: VHJBRD1GN5JL
• Metabolomics Workbench ID: 37659
• ChEMBL ID: CHEMBL384759
• Mol file: 146-91-8.mol

Synonyms:5'-Diphosphate, Guanosine;5'-Trihydrogen Diphosphate, Guanosine;Diphosphate, Guanosine;Diphosphate, Guanosine 5'-Trihydrogen;GDP;Guanosine 5' Diphosphate;Guanosine 5' Trihydrogen Diphosphate;Guanosine 5'-Diphosphate;Guanosine 5'-Trihydrogen Diphosphate;Guanosine Diphosphate

Chemical Property of Guanosine-5'-diphosphate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.94
• Boiling Point: 961 °C at 760 mmHg
• PKA: pK3:2.9;pK4:6.3;pk5:9.6 (25°C,μ=0.1)
• Flash Point: 535 °C
• PSA: 272.19000
• Density: 2.63 g/cm³
• LogP: -1.87150
• Storage Temp.: −20°C
• Solubility.: H2O: 50 mg/mL, clear, colorless
• XLogP3: -4.6
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 6
• Exact Mass: 443.02433031
• Heavy Atom Count: 28
• Complexity: 760

Purity/Quality:

99%, ^*data from raw suppliers

Guanosine5'-diphosphate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: UVCB
• Canonical SMILES: C1=NC2=C(N1C3C(C(C(O3)COP(=O)(O)OP(=O)(O)O)O)O)N=C(NC2=O)N
• Isomeric SMILES: C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)O)O)O)N=C(NC2=O)N
• Recent ClinicalTrials: Safety and Efficacy of Epcoritamab With Gemcitabine, Dexamethasone, and Cisplatin (GDP) Salvage Chemotherapy in Relapsed Refractory Large B-cell Lymphoma
• Uses: Guanosine 5''-Diphosphate is used in methods of modulating immune activity using modulators of STING and purinergic receptors and screening assays.

Technology Process of Guanosine-5'-diphosphate

There total 50 articles about Guanosine-5'-diphosphate 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: 98.0%

Guanosine 5'-monophosphate imidazolide (69281-33-0) → guanosine-5'-diphosphate (146-91-8)

Guidance literature:

With Phosphoric acid tri-n-butylammonium salt; zinc(II) chloride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1080/00397910600941448

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: 84.0%

2-deoxy-2-fluoro-D-mannopyranoside (7226-39-3,7241-17-0,28876-44-0,38711-37-4,55449-80-4,62182-10-9,62182-14-3,86783-82-6,98856-44-1,98856-45-2,98856-46-3,31077-88-0) + Guanosine 5'-triphosphate (86-01-1,72490-81-4) → guanosine-5’-diphospho-2′′-fluoro-α-D-mannopyranosyl (67341-46-2) + guanosine-5'-diphosphate (146-91-8)

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

upstream raw materials:

2',3'-isopropylideneguanosine

Guanosine 5'-monophosphate

ATP

Guanosine 5'-triphosphate

Downstream raw materials:

Guanosine 5'-triphosphate

Guanosine 5'-monophosphate

P¹--P²-<4-morpholin>pyrophosphat

G

Refernces

• 1、 Stern, Noa,Major, Dan Thomas,Gottlieb, Hugo Emilio,Weizman, Daniel,Fischer, Bilha. "What is the conformation of physiologically-active dinucleoside polyphosphates in solution? Conformational analysis of free dinucleoside polyphosphates by NMR and molecular dynamics simulations". . p. 4637 - 4652. Retrieved 2010.
• 2、 Ince, Semra,Zhang, Ping,Kutsch, Miriam,Krenczyk, Oktavian,Shydlovskyi, Sergii,Herrmann, Christian. "Catalytic activity of human guanylate-binding protein 1 coupled to the release of structural restraints imposed by the C-terminal domain". . p. 582 - 599. Retrieved 2021.
• 3、 Wang, Huan,Oman, Trent J.,Zhang, Ran,Garcia De Gonzalo, Chantal V.,Zhang, Qi,Van Der Donk, Wilfred A.. "The glycosyltransferase involved in thurandacin biosynthesis catalyzes both O- and S-glycosylation". . p. 84 - 87. Retrieved 2014.
• 4、 Hasselbach. "-". . p. 355,356,359. Retrieved 1956.
• 5、 Strominger et al.. "-". . p. 412,417. Retrieved 1959.
• 6、 Heppel et al.. "-". . p. 422,427. Retrieved 1959.
• 7、 Chambers,Khorana. "-". . p. 3752,3753,3754. Retrieved 1957.
• 8、 Kanavarioti, Anastassia,Rosenbach, Morgan T.. "Catalysis of Hydrolysis and Nucleophilic Substitution at the P-N Bond of Phosphoimidazolide-Activated Nucleotides in Phosphate Buffers". . p. 1513 - 1521. Retrieved 1991.
• 9、 Uno, Tomohide,Ueno, Mayumi,Nakajima, Ayumi,Shirai, Yasuhito,Aizono, Yasuo. "Molecular Cloning of cDNA for BRab from the Brain of Bombyx mori and Biochemical Properties of BRab Expressed in Escherichia coli". . p. 1885 - 1891. Retrieved 1998.
• 10、 Hasselbach. "-". . p. 365,367,369,371. Retrieved 1957.