Phosphoadenosine phosphosulfate (ECMDB01134) (M2MDB000269)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:46:04 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:53:46 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Phosphoadenosine phosphosulfate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | 3'-Phosphoadenosine-5'-phosphosulfate is a key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from a sulfate ion and ATP in a two-step process. This compound also is an important intermediate in the process of sulfur fixation in plants and microorganisms. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C10H15N5O13P2S | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 507.264 Monoisotopic: 506.986229305 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | GACDQMDRPRGCTN-KQYNXXCUSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C10H15N5O13P2S/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-30(20,21)28-31(22,23)24/h2-4,6-7,10,16H,1H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)(H,22,23,24)/t4-,6-,7-,10-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 482-67-7 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | 3'-phosphoadenylyl sulfate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]1O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as purine ribonucleoside 3',5'-bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Nucleosides, nucleotides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Purine nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Purine ribonucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Purine ribonucleoside 3',5'-bisphosphates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents |
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Substituents |
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Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | glutaredoxin + Phosphoadenosine phosphosulfate > glutaredoxin +2 Hydrogen ion + Adenosine 3',5'-diphosphate + Sulfite Phosphoadenosine phosphosulfate + Reduced Thioredoxin >2 Hydrogen ion + Adenosine 3',5'-diphosphate + Sulfite + Oxidized Thioredoxin Adenosine phosphosulfate + Adenosine triphosphate <> ADP + Hydrogen ion + Phosphoadenosine phosphosulfate Phosphoadenosine phosphosulfate + Water <> Adenosine phosphosulfate + Phosphate Adenosine triphosphate + Adenosine phosphosulfate <> ADP + Phosphoadenosine phosphosulfate Thioredoxin + Phosphoadenosine phosphosulfate + Thioredoxin disulfide <> Thioredoxin disulfide + Sulfite + Adenosine 3',5'-diphosphate + Thioredoxin Adenosine phosphosulfate + Adenosine triphosphate > Hydrogen ion + Phosphoadenosine phosphosulfate + ADP Adenosine triphosphate + Adenosine phosphosulfate > ADP + Phosphoadenosine phosphosulfate Adenosine 3',5'-diphosphate + Sulfite + thioredoxin disulfide > Phosphoadenosine phosphosulfate + thioredoxin Phosphoadenosine phosphosulfate + reduced thioredoxin > Sulfite +2 Hydrogen ion + Adenosine 3',5'-diphosphate +2 oxidized thioredoxin + Sulfite + Adenosine 3',5'-diphosphate Phosphoadenosine phosphosulfate + reduced thioredoxin > Sulfite + oxidized thioredoxin + Hydrogen ion + Adenosine 3',5'-diphosphate + Sulfite + Adenosine 3',5'-diphosphate Adenosine phosphosulfate + Adenosine triphosphate > Phosphoadenosine phosphosulfate + Adenosine diphosphate + Hydrogen ion + ADP Adenosine phosphosulfate + Adenosine triphosphate <> ADP + Hydrogen ion + Phosphoadenosine phosphosulfate Thioredoxin + Phosphoadenosine phosphosulfate + Thioredoxin disulfide <> Sulfite + Adenosine 3',5'-diphosphate Phosphoadenosine phosphosulfate + Water <> Adenosine phosphosulfate + Phosphate Phosphoadenosine phosphosulfate + Water <> Adenosine phosphosulfate + Phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Lin, Chun-Hung; Shen, Gwo-Jenn; Garcia-Junceda, Eduardo; Wong, Chi-Huey. Enzymic Synthesis and Regeneration of 3'-Phosphoadenosine 5'-Phosphosulfate (PAPS) for Regioselective Sulfation of Oligosaccharides. Journal of the American Chemical Society (1995), | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in adenylylsulfate kinase activity
- Specific function:
- Catalyzes the synthesis of activated sulfate
- Gene Name:
- cysC
- Uniprot ID:
- P0A6J1
- Molecular weight:
- 22321
Reactions
ATP + adenylyl sulfate = ADP + 3'-phosphoadenylyl sulfate. |
- General function:
- Involved in electron carrier activity
- Specific function:
- Efficient electron donor for the essential enzyme ribonucleotide reductase. Is also able to reduce the interchain disulfide bridges of insulin
- Gene Name:
- trxC
- Uniprot ID:
- P0AGG4
- Molecular weight:
- 15555
Reactions
Protein dithiol + NAD(P)(+) = protein disulfide + NAD(P)H. |
- General function:
- Involved in phosphoadenylyl-sulfate reductase (thioredoxin) activity
- Specific function:
- Reduction of activated sulfate into sulfite
- Gene Name:
- cysH
- Uniprot ID:
- P17854
- Molecular weight:
- 27976
Reactions
Adenosine 3',5'-bisphosphate + sulfite + thioredoxin disulfide = 3'-phosphoadenylyl sulfate + thioredoxin. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- Converts 3'(2')-phosphoadenosine 5'-phosphate (PAP) to AMP. May also convert adenosine 3'-phosphate 5'-phosphosulfate (PAPS) to adenosine 5'-phosphosulfate (APS). Has 10000-fold lower activity towards inositol 1,4-bisphosphate (Ins(1,4)P2)
- Gene Name:
- cysQ
- Uniprot ID:
- P22255
- Molecular weight:
- 27176
Reactions
Adenosine 3',5'-bisphosphate + H(2)O = adenosine 5'-phosphate + phosphate. |
- General function:
- Involved in transporter activity
- Specific function:
- Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- ssuC
- Uniprot ID:
- P75851
- Molecular weight:
- 28925
- General function:
- Involved in electron carrier activity
- Specific function:
- Monothiol glutaredoxin involved in the biogenesis of iron-sulfur clusters (Probable)
- Gene Name:
- grxD
- Uniprot ID:
- P0AC69
- Molecular weight:
- 12879
- General function:
- Involved in electron carrier activity
- Specific function:
- The disulfide bond functions as an electron carrier in the glutathione-dependent synthesis of deoxyribonucleotides by the enzyme ribonucleotide reductase. In addition, it is also involved in reducing some disulfides in a coupled system with glutathione reductase
- Gene Name:
- grxC
- Uniprot ID:
- P0AC62
- Molecular weight:
- 9137
- General function:
- Involved in protein binding
- Specific function:
- Involved in reducing some disulfides in a coupled system with glutathione reductase. Does not act as hydrogen donor for ribonucleotide reductase
- Gene Name:
- grxB
- Uniprot ID:
- P0AC59
- Molecular weight:
- 24350
- General function:
- Involved in electron carrier activity
- Specific function:
- The disulfide bond functions as an electron carrier in the glutathione-dependent synthesis of deoxyribonucleotides by the enzyme ribonucleotide reductase. In addition, it is also involved in reducing some disulfides in a coupled system with glutathione reductase
- Gene Name:
- grxA
- Uniprot ID:
- P68688
- Molecular weight:
- 9685
- General function:
- Involved in electron carrier activity
- Specific function:
- Participates in various redox reactions through the reversible oxidation of its active center dithiol to a disulfide and catalyzes dithiol-disulfide exchange reactions
- Gene Name:
- trxA
- Uniprot ID:
- P0AA25
- Molecular weight:
- 11807
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- ssuC
- Uniprot ID:
- P75851
- Molecular weight:
- 28925