3'-Adenylic acid

Base Information

• Chemical Name: 3'-Adenylic acid
• CAS No.: 84-21-9
• Molecular Formula: C10H14 N5 O7 P
• Molecular Weight: 347.224
• European Community (EC) Number: 201-521-8
• UNII: R438H7I3KZ
• DSSTox Substance ID: DTXSID40876084
• Nikkaji Number: J36.734F
• Wikidata: Q27103969
• Metabolomics Workbench ID: 38356
• ChEMBL ID: CHEMBL576739
• Mol file: 84-21-9.mol

Synonyms:2' Adenosine Monophosphate;2' Adenylic Acid;2'-adenosine monophosphate;2'-adenylic acid;2'-AMP;5' Adenylic Acid;5'-Adenylic Acid;5'-Phosphate, Adenosine;Acid, 2'-Adenylic;Acid, 5'-Adenylic;Adenosine 2' Phosphate;Adenosine 2'-Phosphate;Adenosine 3' Phosphate;Adenosine 3'-Phosphate;Adenosine 5' Phosphate;Adenosine 5'-Phosphate;Adenosine Monophosphate;Adenosine Phosphate Dipotassium;Adenosine Phosphate Disodium;Adenylic Acid;AMP;Dipotassium, Adenosine Phosphate;Disodium, Adenosine Phosphate;Monophosphate, 2'-Adenosine;Phosphaden;Phosphate Dipotassium, Adenosine;Phosphate Disodium, Adenosine

Chemical Property of 3'-Adenylic acid

Chemical Property:

• Melting Point: ~210 °C (dec.)
• Boiling Point: 815.5oC at 760 mmHg
• PKA: pK1: 3.65(0);pK2: 5.88(-1) (25°C)
• Flash Point: 447oC
• PSA: 195.88000
• Density: 2.32g/cm3
• LogP: -1.28180
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Base (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 0.5g/L(15 oC)
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 347.06308480
• Heavy Atom Count: 23
• Complexity: 481

Purity/Quality:

98%,99%, ^*data from raw suppliers

Adenosine 3′-monophosphate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)OP(=O)(O)O)O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)OP(=O)(O)O)O)N
• Uses: Adenosine 3′-monophosphate (3′-AMP) is a metabolite produced from hydrolysis of 2′,3′-cAMP by a family of metal-dependent phosphodiesterases. 3′-AMP inhibits proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors. 2′,3′-cAMP and 3′-AMP represent a new unexplored pathway for adenosine-based cell regulation.

Technology Process of 3'-Adenylic acid

There total 76 articles about 3'-Adenylic 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:

cAMP (60-92-4) → adenosine monophosphate (84-21-9) + 5'-adenosine monophosphate (61-19-8,24937-83-5,67583-85-1)

Guidance literature:

With cerium(III) chloride; water; at 30 ℃; Rate constant; Mechanism; pH 8.0; velocity const. - var. pH's dependence;

DOI:10.1039/c39920001707

Reference yield:

C10H12Cl2N5O5P (34051-17-7) → C10H15N5O15P4 (68914-00-1) + adenosine monophosphate (84-21-9) + 5'-adenosine monophosphate (61-19-8,24937-83-5,67583-85-1) + adenosine 2'-monophosphate (130-49-4) + 3'-phosphoadenosine-5'-phosphate (1053-73-2) + ATP (56-65-5,896506-78-8)

Guidance literature:

With tributyl-amine; bis(tri-n-butylammonium) pyrophosphate; N,N-dimethyl-formamide; In trimethyl phosphite; at 0 ℃; for 0.0166667h;

DOI:10.1080/15257771003709569

Reference yield:

adenosine (58-61-7) → adenosine monophosphate (84-21-9) + 5'-adenosine monophosphate (61-19-8,24937-83-5,67583-85-1) + adenosine 2',3'-cyclic monophosphate (634-01-5) + adenosine 2'-monophosphate (130-49-4)

Guidance literature:

With hydroxyapatite; ammonium ferrocyanide; water; ammonium formate; urea; at 85 ℃;

DOI:10.1002/anie.201908272

upstream raw materials:

5'-O-(triphenylmethyl)adenosine

pyridine

dibenzyl phosphochloridate

cAMP

Downstream raw materials:

adenosine 2'-monophosphate

[3']adenylic acid monobenzyl ester

adenosine 2',3'-cyclic monophosphate

[3']inosinic acid

Refernces

• 1、 Gillerman, Irina,Fischer, Bilha. "An improved one-pot synthesis of nucleoside 5'-triphosphate analogues". scheme or table. p. 245 - 256. Retrieved 2011/08/06.
• 2、 Urata, Hidehito,Sasaki, Rie,Morita, Hiroyo,Kusumoto, Marina,Ogawa, Yoko,Mitsuda, Kozue,Akagi, Masao. "Kinetic analysis of hydrolytic reaction of homo- and heterochiral adenylyl(3′-5′)adenosine isomers: Breaking homochirality reduces hydrolytic stability of RNA". . p. 2578 - 2580. Retrieved 2007/10/03.