ホスホアデノシンホスホ硫酸
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/11/27 14:30:14」(JST)
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"PAPS" redirects here. For other uses, see Paps (disambiguation).
3'-Phosphoadenosine-5'-phosphosulfate
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| Names |
IUPAC name
6-Amino-9-[(2R,3R,4S,5R)-3-hydroxy-5-
[(hydroxy-sulfooxy-phosphoryl)oxymethyl]
-4-phosphonooxy-tetrahydrofuran-2-yl]purine
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Other names
PAPS
3'-phosphoadenylyl sulfate
phosphoadenosine phosphosulfate
3'-phospho-5'-adenylyl sulfate |
| Identifiers |
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CAS Number
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482-67-7 |
| Abbreviations |
PAPS |
| ChEBI |
CHEBI:17980 |
| ChemSpider |
9799 Y |
InChI
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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 Y
Key: GACDQMDRPRGCTN-KQYNXXCUSA-N Y
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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
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IUPHAR/BPS
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1719 |
| Jmol interactive 3D |
Image
Image |
| PubChem |
10214 |
SMILES
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S=C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)COP(=O)(O)OS(=O)(=O)O)OP(=O)(O)O)O
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O=S(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3OP(=O)(O)O
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| Properties |
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Chemical formula
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C10H15N5O13P2S |
| Molar mass |
507.266 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Y verify (what is YN ?) |
| Infobox references |
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3'-Phosphoadenosine-5'-phosphosulfate is a derivative of adenosine monophosphate that is phosphorylated at the 3' position and has a sulfate group attached to the 5' phosphate. This anion, abbreviated PAPS, is the most common coenzyme in sulfotransferase reactions. A related anion is adenosine 5'-phosphosulfate (APS), which is not phosphorylated at the 3' position.[1]
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 sulfurase:
- SO42− + ATP → APS + PPi
The conversion of APS to PAPS is catalysed by APS kinase:
- APS + ATP → PAPS + ADP
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.[2]
References
- ^ 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.
- ^ M. T. Madigan, J. M. Martinko, J. Parker “Brock Biology of Microorganisms” Prentice Hall, 1997. ISBN 0-13-520875-0.
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Enzyme cofactors
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| Active forms |
| vitamins |
- TPP / ThDP (B1)
- FMN, FAD (B2)
- NAD+, NADH, NADP+, NADPH (B3)
- Coenzyme A (B5)
- PLP / P5P (B6)
- Biotin (B7)
- THFA / H4FA, DHFA / H2FA, MTHF (B9)
- AdoCbl, MeCbl (B12)
- Ascorbic acid (C)
- Phylloquinone (K1), Menaquinone (K2)
- Coenzyme F420
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| non-vitamins |
- ATP
- CTP
- SAMe
- PAPS
- GSH
- Coenzyme B
- Cofactor F430
- Coenzyme M
- Coenzyme Q
- Heme / Haem (A, B, C, O)
- Lipoic Acid
- Methanofuran
- Molybdopterin/Molybdenum cofactor
- PQQ
- THB / BH4
- THMPT / H4MPT
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| minerals |
- Ca2+
- Cu2+
- Fe2+, Fe3+
- Mg2+
- Mn2+
- Mo
- Ni2+
- Zn2+
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| Base forms |
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Index of nutrition
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| Description |
- Vitamins
- Cofactors
- Metal metabolism
- Fats
- metabolism
- intermediates
- lipoproteins
- Sugars
- Glycolysis
- Glycogenesis and glycogenolysis
- Fructose and galactose
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| Disease |
- Vitamins
- Carbohydrate
- Lipid
- Metals
- Other
- Symptoms and signs
- Tests
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| Treatment |
- Drugs
- Vitamins
- Mineral supplements
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UpToDate Contents
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English Journal
- Design and Interpretation of Human Sulfotransferase A1 Assays.
- Wang T1, Cook I1, Leyh TS2.
- Drug metabolism and disposition: the biological fate of chemicals.Drug Metab Dispos.2016 Apr;44(4):481-4. doi: 10.1124/dmd.115.068205. Epub 2015 Dec 9.
- The human sulfotransferases (SULTs) regulate the activities of hundreds, if not thousands, of small molecule metabolites via transfer of the sulfuryl-moiety (-SO3) from the nucleotide donor, 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to the hydroxyls and amines of the recipients. Our understanding
- PMID 26658224
- Heparan sulfation is essential for the prevention of cellular senescence.
- Jung SH1,2,3, Lee HC1,2, Yu DM4, Kim BC3, Park SM3, Lee YS5, Park HJ2,6, Ko YG4, Lee JS1,2.
- Cell death and differentiation.Cell Death Differ.2016 Mar;23(3):417-29. doi: 10.1038/cdd.2015.107. Epub 2015 Aug 7.
- Cellular senescence is considered as an important tumor-suppressive mechanism. Here, we demonstrated that heparan sulfate (HS) prevents cellular senescence by fine-tuning of the fibroblast growth factor receptor (FGFR) signaling pathway. We found that depletion of 3'-phosphoadenosine 5'-phosphosulfa
- PMID 26250908
- Human liver cytosolic sulfotransferase 2A1-dependent dehydroepiandrosterone sulfation assay by ultra-high performance liquid chromatography-tandem mass spectrometry.
- Bansal S1, Lau AJ2.
- Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2016 Feb 20;120:261-9. doi: 10.1016/j.jpba.2015.12.029. Epub 2015 Dec 22.
- Sulfotransferase 2A1 (SULT2A1) is a major catalyst of the sulfation of dehydroepiandrosterone (DHEA) to dehydroepiandrosterone sulfate (DHEA-S) in human liver cytosol. However, there is a lack of a sensitive and fast analytical method for the human liver cytosolic SULT2A1-dependent DHEA sulfation as
- PMID 26760244
Japanese Journal
- Cloning, Expression, and Characterization of Cytosolic Sulfotransferase Isozymes from Drosophila melanogaster
- HATTORI Kenji,MOTOHASHI Noriko,KOBAYASHI Izumi,TOHYA Takeshi,OIKAWA Mai,TAMURA Hiro-omi
- Bioscience, biotechnology, and biochemistry 72(2), 540-547, 2008-02-23
- … DmST4 and dmST3 showed the lowest and highest Km values for 3′-phosphoadenosine-5′-phosphosulfate (PAPS) respectively. …
- NAID 10027524657
- Characterization of in vitro metabolites of toad venom using high-performance liquid chromatography and liquid chromatography - Mass spectrometry
- Shimada Kazutake,Miyashiro Yoshimichi,Nishio Tadashi
- Biomedical Chromatography 20(12), 1321-1327, 2006-12
- … Marinobufagin produced its 3-sulfate upon treatment with the rat or human liver cytosolic fraction and 3′-phosphoadenosine 5′-phosphosulfate. …
- NAID 120000810087
Related Links
- 3'-Phosphoadenosine-5'-phosphosulfate is a derivative of adenosine monophosphate that is phosphorylated at the 3' position and has a sulfate group attached to the 5' phosphate. This anion, abbreviated PAPS, is the most common coenzyme ...
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