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A5763

Sigma-Aldrich

Adenosine 3′,5′-diphosphate disodium salt

≥96%

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:
Molecular Weight:
471.16
MDL number:
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (inorganic)

Quality Level

Assay

≥96%

form

powder

solubility

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

storage temp.

−20°C

SMILES string

[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);;

InChI key

ISROZYFZEAVMSP-UHFFFAOYSA-N

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.

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Hao Chen et al.
Plant, cell & environment, 33(12), 2180-2190 (2010-09-03)
The Arabidopsis FIERY1 (FRY1) locus was originally identified as a negative regulator of stress-responsive gene expression and later shown to be required for suppression of RNA silencing. In this study we discovered that the FRY1 locus also regulates lateral root
3?-phosphoadenosine 5?-phosphate accumulation delays the circadian system
Litthauer S, et al.
Plant Physiology, 176(4), 3120-3135 (2018)
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
A single amino acid substitution in the Arabidopsis FIERY1/HOS2 protein confers cold signaling specificity and lithium tolerance
Xiong L, et al.
The Plant Journal, 40(4), 536-545 (2004)

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