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3'-Phosphoadenosine-5'-phosphosulfate

From Wikipedia, the free encyclopedia
"PAPS" redirects here. For other uses, seePaps (disambiguation).
3′-Phosphoadenosine-5′-phosphosulfate
Names
IUPAC name
3′-O-Phosphono-5′-adenylyl hydrogen sulfate
Systematic IUPAC name
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl hydrogen (sulfooxy)phosphonate
Other names
PAPS
3′-Phosphoadenylyl sulfate
Phosphoadenosine phosphosulfate
3′-Phospho-5′-adenylyl sulfate
Identifiers
3D model (JSmol)
AbbreviationsPAPS
ChEBI
ChemSpider
ECHA InfoCard100.222.927Edit this at Wikidata
EC Number
  • 694-699-5
KEGG
UNII
  • 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 checkY
    Key: GACDQMDRPRGCTN-KQYNXXCUSA-N checkY
  • InChI=1/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
    Key: GACDQMDRPRGCTN-KQYNXXCUBK
  • 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
Properties
C10H15N5O13P2S
Molar mass507.266
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

3′-Phosphoadenosine-5′-phosphosulfate (PAPS) is a derivative ofadenosine monophosphate (AMP) that isphosphorylated at the 3′ position and has asulfate group attached to the 5′phosphate. It is the most commoncoenzyme insulfotransferase reactions and hence part ofsulfation pathways.[1] It is endogenously synthesized by organisms via the phosphorylation of adenosine 5′-phosphosulfate (APS), an intermediary metabolite.[2] In humans such reaction is performed by bifunctional 3′-phosphoadenosine 5′-phosphosulfate synthases (PAPSS1 andPAPSS2) usingATP as the phosphate donor.[3][4]

Formation and reduction

[edit]

APS and PAPS are intermediates in the reduction of sulfate tosulfite, an exothermic conversion that is carried out bysulfate-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 byATP sulfurylase:

SO42− + ATP ⇌ APS + PPi

The conversion of APS to PAPS is catalysed byAPS kinase:

APS + ATP ⇌ PAPS + ADP
Structure of adenosine 5′-phosphosulfate (APS).

Reduction of APS leads to sulfite, which is further reduced tohydrogen sulfide, which is excreted. This process is called dissimilatory sulfate reduction. Reduction of PAPS, a more elaboratedsulfate ester, leads also to hydrogen sulfide. But in this case, the product is used in biosynthesis, e.g. for the production ofcysteine. The latter process is called assimilatory sulfate reduction because the sulfate sulfur is assimilated.[5]

References

[edit]
  1. ^Günal S; Hardman R; Kopriva S; Mueller JW (2019)."Sulfation pathways from red to green".J. Biol. Chem.294 (33):12293–12312.doi:10.1074/jbc.REV119.007422.PMC 6699852.PMID 31270211.
  2. ^Negishi M; Pedersen LG; Petrotchenko E; et al. (2001)."Structure and function of sulfotransferases".Arch. Biochem. Biophys.390 (2):149–57.doi:10.1006/abbi.2001.2368.PMID 11396917.
  3. ^Xu, Zhen-Hua; Otterness, Diane M.; Freimuth, Robert R.; Carlini, Edward J.; Wood, Thomas C.; Mitchell, Steve; Moon, Eunpyo; Kim, Ung-Jin; Xu, Jing-Ping; Siciliano, Michael J.; Weinshilboum, Richard M. (February 2000). "Human 3′-Phosphoadenosine 5′-Phosphosulfate Synthetase 1 (PAPSS1) and PAPSS2: Gene Cloning, Characterization and Chromosomal Localization".Biochemical and Biophysical Research Communications.268 (2):437–444.doi:10.1006/bbrc.2000.2123.PMID 10679223.
  4. ^Venkatachalam, K. V. (2003)."Human 3′-phosphoadenosine 5′-phosphosulfate (PAPS) synthase: Biochemistry, molecular biology and genetic deficiency".IUBMB Life.55 (1):1–11.doi:10.1080/1521654031000072148.PMID 12716056.S2CID 37733913.
  5. ^M. T. Madigan, J. M. Martinko, J. Parker “Brock Biology of Microorganisms” Prentice Hall, 1997.ISBN 0-13-520875-0.
Active forms
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non-vitamins
metal ions
Base forms
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