A3013

Adenosine 2′(3′)-monophosphate mixed isomers

• Synonym(s): Yeast adenylic acid
• Empirical Formula (Hill Notation): C₁₀H₁₄N₅O₇P
• CAS Number: 130-49-4
• Molecular Weight: 347.22
• EC Number: 204-990-7
• MDL number: MFCD00151215
• UNSPSC Code: 41106305
• PubChem Substance ID: 24890716
• NACRES: NA.51

Properties

• biological source: synthetic
• assay: ≥45% (Adenosine-3′-monophosphate, HPLC); ≥97% (Total Adenosine-3′-monophosphate; Adenosine-2′-monophosphate, HPLC); 10-55% ( Adenosine-2′-monophosphate, HPLC)
• form: powder
• solubility: 1 M NH4OH: 50 mg/mL, clear, colorless
• storage temp.: −20°C
• SMILES string: Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H]3O.Nc4ncnc5n(cnc45)[C@@H]6O[C@H](CO)[C@@H](O)[C@H]6OP(O)(O)=O
• InChI: 1S/2C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(17)7(4(1-16)21-10)22-23(18,19)20;11-8-5-9(13-2-12-8)15(3-14-5)10-7(22-23(18,19)20)6(17)4(1-16)21-10/h2*2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t2*4-,6-,7-,10-/m11/s1
• InChI key: UQRXDDDXDPEXNS-VQFZJOCSSA-N

Description

General description

Adenosine 3′-monophosphate (3′-AMP) and Adenosine 2′-monophosphate (2′-AMP) are metabolites produced from hydrolysis of 2′,3′-cAMP by a family of metal-dependent phosphodiesterases. 2′-AMP and 3′-AMP inhibit proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors.

Application

Adenosine2′(3′)-monophosphate mixed isomers have been used as a standard to separate andquantify purines (adenine and guanine) and adenine ribonucleosidemonophosphates (2’-AMP and 3’-AMP) through isocratic high-performance liquidchromatography (HPLC). It has also been used to screen the multiplesugar-binding ATPase A (MsbA) transporter protein.

Linkage

Do not confuse with adenosine 2′:3′-cyclic monophosphate

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable