{[(2R,3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid

Base Information

• Chemical Name: {[(2R,3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
• CAS No.: 41708-91-2
• Molecular Formula: C20H29N10O22P5
• Molecular Weight: 916.373
• Metabolomics Workbench ID: 37653
• Mol file: 41708-91-2.mol

Synonyms:CHEBI:184894;({[({[(2R,3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)({[({[(3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid;[[(2R,3S,4R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[[(3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate;{[(2R,3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid

Chemical Property of {[(2R,3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid

Chemical Property:

• PSA: 529.55000
• LogP: -1.16700
• XLogP3: -9.4
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 30
• Rotatable Bond Count: 16
• Exact Mass: 916.01459758
• Heavy Atom Count: 57
• Complexity: 1580

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)N5C=NC6=C(N=CN=C65)N)O)O)O)O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H](C(O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@@H]4[C@H]([C@H](C(O4)N5C=NC6=C(N=CN=C65)N)O)O)O)O)N

Technology Process of {[(2R,3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid

There total 5 articles about {[(2R,3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)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: 80.0%

ATP (56-65-5,896506-78-8) + adenosine 5'-tetraphosphate (1062-98-2) → p1,p5-di(adenosine 5'-)pentaphosphate (41708-91-2)

Guidance literature:

With LEUCINE; In various solvent(s); at 40 ℃; at pH 7.5; ATP-regenerating system of acetate kinase, adenylate kinase, PPase with acetyl phosphate;

Reference yield:

adenosine 5'-trimetaphosphate (53355-60-5) + tris(tributylammonio)-ADP (73763-39-0) → P1,P6-di(adenosine-5') hexaphosphate (56983-23-4) + Diadenosine tetraphosphate (5542-28-9,117137-55-0) + p1,p5-di(adenosine 5'-)pentaphosphate (41708-91-2)

Guidance literature:

In N,N-dimethyl-formamide; at 35 ℃; for 18h; Yields of byproduct given;

DOI:10.1021/jm00348a006

Reference yield:

ATP (56-65-5,896506-78-8) → p1,p5-di(adenosine 5'-)pentaphosphate (41708-91-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / P₃, leucin, LeuRS / various solvent(s) / 40 °C / at pH 7.5; ATP-regenerating system of acetate kinase, adenylate kinase, PPase with acetyl phosphate

2: 80 percent / leucin, LeuRS / various solvent(s) / 40 °C / at pH 7.5; ATP-regenerating system of acetate kinase, adenylate kinase, PPase with acetyl phosphate

With LEUCINE; In various solvent(s);

upstream raw materials:

adenosine 5'-trimetaphosphate

tris(tributylammonio)-ADP

ATP

adenosine 5'-tetraphosphate

Downstream raw materials:

adenosine 5'-diphosphate

ATP

P¹,P⁵-diadenosine-5′,5′-pentaphosphate pentasodium salt

Refernces

• 1、 Nakajima, Hiroshi,Tomioka, Isao,Kitabatake, Senji,Dombou, Munehiko,Tomita, Kosuke. "Facile and Selective Synthesis of Diadenosine Polyphosphates through Catalysis by Leucyl t-RNA Synthetase Coupled with ATP Regeneration". . p. 615 - 624. Retrieved 2007/10/02.