A9396

Adenosine 2′-monophosphate

from yeast

• Synonym(s): Adenosine 2′-monophosphoric acid, phosphoadenosine, 2′-AMP, 2′-Adenylic acid
• Empirical Formula (Hill Notation): C₁₀H₁₄N₅O₇P
• CAS Number: 130-49-4
• Molecular Weight: 347.22
• UNSPSC Code: 41106305
• eCl@ss: 32160414
• PubChem Substance ID: 24891443
• NACRES: NA.51

Properties

• biological source: yeast
• assay: ≥98% (HPLC)
• form: powder
• solubility: 1 N NH₄OH: 50 mg/mL, clear, colorless to faintly yellow
• storage temp.: −20°C
• SMILES string: NC1=NC=NC2=C1N=CN2[C@H]3[C@H](OP(O)(O)=O)[C@H](O)[C@@H](CO)O3.[H]O[H].NC4=NC=NC5=C4N=CN5[C@H]6[C@H](OP(O)(O)=O)[C@H](O)[C@@H](CO)O6
• InChI: 1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(22-23(18,19)20)6(17)4(1-16)21-10/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
• InChI key: QDFHPFSBQFLLSW-KQYNXXCUSA-N

Description

General description

Adenosine 2′-monophosphate (2’-AMP) is an adenine nucleotide having single phosphate group esterified to the sugar moiety in the 2′-position.

Application

Adenosine 2′-monophosphate (2′-AMP) is a metabolite produced from hydrolysis of 2′,3′-cAMP. 2′-AMP inhibits proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors. 2′-AMP is used in the synthesis of a new photoaffinity lable for the coenzyme site of porcine NADP-specific isocitrate dehydrogenase. 2′,3′-cAMP and 2′-AMP represent a new unexplored pathway for adenosine-based cell regulation.

Biochem/physiol Actions

AMP serves as a key component of several compounds, including coenzyme A, which plays an essential role in energy metabolism, as well as certain key redox cofactors such as NAD⁺, NADP⁺, and FAD. Furthermore, AMP is one of the key components of RNA, which is essential for protein synthesis and other biological processes in cells.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)