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Merck
CN

A5763

Adenosine 3′,5′-diphosphate disodium salt

≥96%, synthetic (inorganic), powder

Synonym(s):

3′-phosphoadenosine 5′-phosphate, 3′-phosphorylated nucleotide, PAP, 3′-Phosphoadenosine 5′-phosphate

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About This Item

Empirical Formula (Hill Notation):
C10H13N5Na2O10P2
CAS Number:
75431-54-8
Molecular Weight:
471.16
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
24891020
NACRES:
NA.51
MDL number:
MFCD00057007

Key Documents

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Product Name

Adenosine 3′,5′-diphosphate disodium salt, ≥96%

SMILES string

[Na].Nc1ncnc2n(cnc12)C3OC(COP(O)(O)=O)C(OP(O)(O)=O)C3O

InChI key

ISROZYFZEAVMSP-UHFFFAOYSA-N

InChI

1S/C10H15N5O10P2.Na.H/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19;;/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22);;

biological source

synthetic (inorganic)

assay

≥96%

form

powder

solubility

water: 25 mg/mL, clear, colorless to very faintly yellow

storage temp.

−20°C

Quality Level

200

Related Categories

Application

Adenosine 3′,5′-diphosphate disodium salt has been used:
  • to spot sample on cellulose high-performance thin-layer chromatography (HPTLC) plates in two-dimensional thin layer chromatography
  • in enzyme activity assay to study the activities of HOS2/FIERY1 wild type
  • hos2 mutant and fiery1?2 mutant protein against 3′-phosphoadenosine 5′-phosphate (PAP)
  • as a standard for the quantification of phosphoadenosines

Biochem/physiol Actions

3′-phosphoadenosine 5′-phosphate (PAP) is capable of blocking exoribonucleases (XRNs) activity in the nucleus and cytosol. It stimulates stomatal closure and can serve as a secondary messenger during abscisic acid (ABA) signaling. It is capable of blocking RNA catabolism. Hence it may serve as a physiological modulator of poly (ADP-ribose) polymerase 1 (PARP1) activity.
Adenosine 3′,5′-diphosphate (PAP) is used to study the kinetics and mechanisms of hydroxysteroid sulfotransferases such as SULT1A1, SULT2A1 of which it is product inhibitor.

General description

3′-phosphoadenosine 5′-phosphate (PAP), a 3′-phosphorylated nucleotide is found in almost all organisms and is obtained as a by-product of sulfur and lipid metabolism.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000422251
0000422246
0000422251
0000422246
0000403265

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Zhihao Yu et al.
Biochemistry, 47(48), 12777-12786 (2008-11-11)
Most assimilatory bacteria, fungi, and plants species reduce sulfate (in the activated form of APS or PAPS) to produce reduced sulfur. In yeast, PAPS reductase reduces PAPS to sulfite and PAP. Despite the difference in substrate specificity and catalytic cofactor
3?-phosphoadenosine 5?-phosphate accumulation delays the circadian system
Litthauer S, et al.
Plant Physiology, 176(4), 3120-3135 (2018)
Hayrettin Ozan Gulcan et al.
Archives of biochemistry and biophysics, 507(2), 232-240 (2010-12-29)
The cytosolic sulfotransferase hSULT2A1 is the major hydroxysteroid (alcohol) sulfotransferase in human liver, and it catalyzes the 3'-phosphoadenosine-5'-phosphosulfate (PAPS)-dependent sulfation of various endogenous hydroxysteroids as well as many xenobiotics that contain alcohol and phenol functional groups. The hSULT2A1 often displays
Bok-Rye Lee et al.
PloS one, 7(6), e39425-e39425 (2012-06-23)
The fou8 loss of function allele of adenosine bisphosphate phosphatase FIERY1 results in numerous phenotypes including the increased enzymatic oxygenation of fatty acids and increased jasmonate synthesis. Here we show that the mutation causes also profound alterations of sulfur metabolism.
Yungang Liu et al.
Chemico-biological interactions, 189(3), 153-160 (2010-12-07)
Hydroxylated metabolites of polychlorinated biphenyls (OHPCBs) interact with rat sulfotransferase 1A1 (rSULT1A1) as substrates and inhibitors. Previous studies have shown that there are complex and incompletely understood structure-activity relationships governing the interaction of rSULT1A1 with these molecules. Furthermore, modification of
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