Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 3'-Phosphoadenosine-5'-phosphosulfate: Difference between pages - Misplaced Pages

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Difference between pages)
Page 1
Page 2
Content deleted Content addedVisualWikitext
Revision as of 17:40, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443315946 of page 3'-Phosphoadenosine-5'-phosphosulfate for the Chem/Drugbox validation project (updated: '').  Latest revision as of 11:07, 13 January 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,042 edits Altered pages. Formatted dashes. 
Line 1: Line 1:
{{Redirect|PAPS|other uses|Paps (disambiguation)}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 399302364
| Watchedfields = changed
⚫ |ImageFile=3'-Phosphoadenosine-5'-phosphosulfate.svg
⚫ | verifiedrevid = 477216937
⚫ |ImageSize=200px
| Name = 3′-Phosphoadenosine-5′-phosphosulfate
|IUPACName=<small>6-Amino-9-[(''2R,3R,4S,5R'')-3-hydroxy-5-
⚫ | ImageFile=3'-Phosphoadenosine-5'-phosphosulfate.svg
⚫ | ImageSize=200px
-4-phosphonooxy-tetrahydrofuran-2-yl]purine
|OtherNames=Phosphoadenosine phosphosulfate<br>3'-Phospho-5'-adenylyl sulfate</small> | IUPACName=3′-''O''-Phosphono-5′-adenylyl hydrogen sulfate
| SystematicName=methyl hydrogen (sulfooxy)phosphonate
⚫ |Abbreviations=PAPS
| OtherNames=PAPS<br>3′-Phosphoadenylyl sulfate<br>Phosphoadenosine phosphosulfate<br>3′-Phospho-5′-adenylyl sulfate
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo= 482-67-7
⚫ | Abbreviations = PAPS
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | ChEBI = 17980
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9799 | ChemSpiderID = 9799
| EINECS = 694-699-5
| KEGG = C00053
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5TH3ERG159
⚫ | PubChem=10214
⚫ | IUPHAR_ligand = 1719
| 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 | 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
| InChIKey = GACDQMDRPRGCTN-KQYNXXCUBK | InChIKey = GACDQMDRPRGCTN-KQYNXXCUBK
| SMILES1 = O=S(=O)(O)OP(=O)(O)OC3O(n2cnc1c(ncnc12)N)(O)3OP(=O)(O)O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GACDQMDRPRGCTN-KQYNXXCUSA-N | StdInChIKey = GACDQMDRPRGCTN-KQYNXXCUSA-N
| SMILES = C1=NC2=C(C(=N1)N)N=CN23(((O3)COP(=O)(O)OS(=O)(=O)O)OP(=O)(O)O)O
⚫ | CASNo=
⚫ }}
⚫ | PubChem=10214
⚫ |Section2={{Chembox Properties
⚫ | IUPHAR_ligand = 1719
⚫ | Formula=C<sub>10</sub>H<sub>15</sub>N<sub>5</sub>O<sub>13</sub>P<sub>2</sub>S
⚫ | ChEBI = 17980
⚫ | MolarMass=507.266
| SMILES=S=<small>C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)
⚫ | Appearance=
COP(=O)(O)OS(=O)(=O)O)OP(=O)(O)O)O</small>
⚫ | Density=
⚫ }}
⚫ | MeltingPt=
⚫ |Section2= {{Chembox Properties
⚫ | BoilingPt=
⚫ | Formula=C<sub>10</sub>H<sub>15</sub>N<sub>5</sub>O<sub>13</sub>P<sub>2</sub>S
⚫ | Solubility=
⚫ | MolarMass=507.266
⚫ | Appearance=
⚫ | Density=
⚫ | MeltingPt=
⚫ | BoilingPt=
⚫ | Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}

'''3′-Phosphoadenosine-5′-phosphosulfate''' ('''PAPS''') is a derivative of ] (AMP) that is ] at the 3′ position and has a ] group attached to the 5′ ]. It is the most common ] in ] reactions and hence part of ].<ref>{{cite journal |author =Günal S |author2 =Hardman R |author3 =Kopriva S |author4 =Mueller JW |title=Sulfation pathways from red to green |journal=J. Biol. Chem. |volume=294 |issue=33 |pages=12293–12312 |year=2019 |pmid=31270211 |doi=10.1074/jbc.REV119.007422|doi-access=free |pmc=6699852 }}</ref> It is endogenously synthesized by organisms via the phosphorylation of adenosine 5′-phosphosulfate (APS), an intermediary metabolite.<ref>{{cite journal |author =Negishi M |author2 =Pedersen LG |author3 =Petrotchenko E |title=Structure and function of sulfotransferases |journal=Arch. Biochem. Biophys. |volume=390 |issue=2 |pages=149–57 |year=2001 |pmid=11396917 |doi=10.1006/abbi.2001.2368|url =https://zenodo.org/record/1229406 |display-authors=etal}}</ref> In humans such reaction is performed by bifunctional 3′-phosphoadenosine 5′-phosphosulfate synthases (] and ]) using ] as the phosphate donor.<ref>{{cite journal|last1=Xu|first1=Zhen-Hua|last2=Otterness|first2=Diane M.|last3=Freimuth|first3=Robert R.|last4=Carlini|first4=Edward J.|last5=Wood|first5=Thomas C.|last6=Mitchell|first6=Steve|last7=Moon|first7=Eunpyo|last8=Kim|first8=Ung-Jin|last9=Xu|first9=Jing-Ping|last10=Siciliano|first10=Michael J.|last11=Weinshilboum|first11=Richard M.|title=Human 3′-Phosphoadenosine 5′-Phosphosulfate Synthetase 1 (PAPSS1) and PAPSS2: Gene Cloning, Characterization and Chromosomal Localization|journal=Biochemical and Biophysical Research Communications|date=February 2000|volume=268|issue=2|pages=437–444|doi=10.1006/bbrc.2000.2123|pmid=10679223}}</ref><ref>{{cite journal |last1=Venkatachalam |first1=K. V. |date=2003 |title=Human 3′-phosphoadenosine 5′-phosphosulfate (PAPS) synthase: Biochemistry, molecular biology and genetic deficiency |journal=IUBMB Life |volume=55 |issue=1 |pages=1–11 |doi=10.1080/1521654031000072148 |doi-access=free |pmid=12716056 |s2cid=37733913 |s2cid-access=free}}</ref>

==Formation and reduction==
APS and PAPS are intermediates in the reduction of sulfate to ], an exothermic conversion that is carried out by ]. In these organisms, sulfate serves as an electron acceptor, akin to the use of O<sub>2</sub> 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 ]:
:SO<sub>4</sub><sup>2−</sup> + ATP ⇌ APS + PP<sub>i</sub>
The conversion of APS to PAPS is catalysed by ]:
:APS + ATP ⇌ PAPS + ADP
]
Reduction of APS leads to sulfite, which is further reduced to ], which is excreted. This process is called dissimilatory sulfate reduction. Reduction of PAPS, a more elaborated ], leads also to hydrogen sulfide. But in this case, the product is used in biosynthesis, e.g. for the production of ]. The latter process is called assimilatory sulfate reduction because the sulfate sulfur is assimilated.<ref>M. T. Madigan, J. M. Martinko, J. Parker “Brock Biology of Microorganisms” Prentice Hall, 1997. {{ISBN|0-13-520875-0}}.</ref>

==References==
{{reflist}}

{{Enzyme cofactors}}

{{DEFAULTSORT:Phosphoadenosine-5'-phosphosulfate, 3'-}}
]
]
]
]