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A9396

Adenosine 2′-monophosphate

Name: Adenosine 2&#8242;-monophosphate
Brand: SIGMA

≥98% (HPLC), yeast, powder

Synonym(s):

Adenosine 2′-monophosphoric acid, phosphoadenosine, 2′-AMP, 2′-Adenylic acid

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About This Item

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

Assay:

≥98% (HPLC)

Biological source:

yeast

Form:

powder

Solubility:

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

Storage temp.:

−20°C

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Properties

Product Name

Adenosine 2′-monophosphate, from yeast

biological source

yeast

Quality Segment

200

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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