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Key Documents

A5763

Sigma-Aldrich

Adenosine 3′,5′-diphosphate disodium salt

≥96%

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C10H13N5Na2O10P2
Numéro CAS:
Poids moléculaire :
471.16
Numéro MDL:
Code UNSPSC :
41106305
eCl@ss :
32160414
ID de substance PubChem :
Nomenclature NACRES :
NA.51

Source biologique

synthetic (inorganic)

Niveau de qualité

Pureté

≥96%

Forme

powder

Solubilité

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

Température de stockage

−20°C

Chaîne SMILES 

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

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);;

Clé InChI

ISROZYFZEAVMSP-UHFFFAOYSA-N

Description générale

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.

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves


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Consulter la Bibliothèque de documents

3?-phosphoadenosine 5?-phosphate accumulation delays the circadian system
Litthauer S, et al.
Plant Physiology, 176(4), 3120-3135 (2018)
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.
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
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
Hao Chen et al.
PloS one, 6(10), e26661-e26661 (2011-10-27)
Abiotic stress, such as drought and high salinity, activates a network of signaling cascades that lead to the expression of many stress-responsive genes in plants. The Arabidopsis FIERY1 (FRY1) protein is a negative regulator of stress and abscisic acid (ABA)

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