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3'-phosphoadenosine 5'-phosphosulfate

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EntityQ229811· pop 15· linked from 193 articles

3'-phosphoadenosine 5'-phosphosulfate

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Also known as 3'-phosphoadenosine-5'-phosphosulfate, adenosine-3'-phosphate-5' -phosphosulfate, phosphoadenosine phosphosulfate (PAPS)

3′-Phosphoadenosine-5′-phosphosulfate (PAPS) is a derivative of adenosine monophosphate (AMP) that is phosphorylated at the 3′ position and has a sulfate group attached to the 5′ phosphate. It is the most common coenzyme in sulfotransferase reactions and hence part of sulfation pathways. It is endogenously synthesized by organisms via the phosphorylation of adenosine 5′-phosphosulfate (APS), an intermediary metabolite. In humans such reaction is performed by bifunctional 3′-phosphoadenosine 5′-phosphosulfate synthases (PAPSS1 and PAPSS2) using ATP as the phosphate donor.

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Vinony's link graph records 193 inbound references to 3'-phosphoadenosine 5'-phosphosulfate, and connects out to cofactor, iron and copper.

Vinony files it under Chembox image size set, Coenzymes and ECHA InfoCard ID from Wikidata.

Vinony links it to 14 Wikipedia language editions.

Chemical data

Formula
C10H15N5O13P2S
Molecular weight
507.27 g/mol
IUPAC name
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methyl sulfo hydrogen phosphate
SMILES
C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OS(=O)(=O)O)OP(=O)(O)O)O)N
InChIKey
GACDQMDRPRGCTN-KQYNXXCUSA-N
XLogP
-5
Polar surface area
284 Ų
H-bond donors
6
H-bond acceptors
17
Formal charge
0

via PubChem

Wikidata facts

Has part
carbon
Mass
506.986
Show 5 more facts
chemical formula
C₁₀H₁₅N₅O₁₃P₂S
isomeric SMILES
C1=NC2=C(C(=N1)N)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OS(=O)(=O)O)OP(=O)(O)O)O
canonical SMILES
C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)COP(=O)(O)OS(=O)(=O)O)OP(=O)(O)O)O
found in taxon
Homo sapiens
Commons category
3'-Phosphoadenosine-5'-phosphosulfate
Sources (2)

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Encyclopedic overview

2 sections
Contents
  • Formation and reduction
  • References

3′-Phosphoadenosine-5′-phosphosulfate (PAPS) is a derivative of adenosine monophosphate (AMP) that is phosphorylated at the 3′ position and has a sulfate group attached to the 5′ phosphate. It is the most common coenzyme in sulfotransferase reactions and hence part of sulfation pathways. It is endogenously synthesized by organisms via the phosphorylation of adenosine 5′-phosphosulfate (APS), an intermediary metabolite. In humans such reaction is performed by bifunctional 3′-phosphoadenosine 5′-phosphosulfate synthases (PAPSS1 and PAPSS2) using ATP as the phosphate donor.

==Formation and reduction== APS and PAPS are intermediates in the reduction of sulfate to sulfite, an exothermic conversion that is carried out by sulfate-reducing bacteria. In these organisms, sulfate serves as an electron acceptor, akin to the use of O2 as an electron acceptor by aerobic organisms. Sulfate is not reduced directly but must be activated by the formation of APS or PAPS. These carriers of activated sulfate are produced by reaction with ATP. The first reaction is catalysed by ATP sulfurylase: SO42− + ATP ⇌ APS + PPi The conversion of APS to PAPS is catalysed by APS kinase: APS + ATP ⇌ PAPS + ADP thumb|left|Structure of adenosine 5′-phosphosulfate (APS). Reduction of APS leads to sulfite, which is further reduced to hydrogen sulfide, which is excreted. This process is called dissimilatory sulfate reduction. Reduction of PAPS, a more elaborated sulfate ester, leads also to hydrogen sulfide. But in this case, the product is used in biosynthesis, e.g. for the production of cysteine. The latter process is called assimilatory sulfate reduction because the sulfate sulfur is assimilated.

Excerpted from Wikipedia’s “3'-phosphoadenosine 5'-phosphosulfate” article, available under the CC BY-SA 4.0 licence.

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