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A9396

Sigma-Aldrich

Adenosine 2′-monophosphate

from yeast

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

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

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This Item
A9272A2252A1752
assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥97%

assay

≥99%

form

powder

form

powder

form

powder

form

powder

solubility

1 N NH4OH: 50 mg/mL, clear, colorless to faintly yellow

solubility

1 N NH4OH: 50 mg/mL, clear, colorless

solubility

1 M NH4OH: soluble 50 mg/mL, clear, colorless, H2O: soluble (with addition of mild alkali)

solubility

H2O: soluble

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

300

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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