Synonym:Methylthioadenosine;MTA;5Deoxy5(methylthio)adenosine.

IUPAC/ChemicalName:(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol

InChiKey:WUUGFSXJNOTRMR-IOSLPCCCSA-N

InChiCode:InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h4-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1

SMILESCode:O[C@H]1[C@H](N2C=NC3=C(N)N=CN=C23)O[C@H](CSC)[C@H]1O

TechnicalData

AdditionalInformation

References

1:BertinoJR,WaudWR,ParkerWB,LubinM.Targetingtumorsthatlackmethylthioadenosinephosphorylase(MTAP)activity:currentstrategies.CancerBiolTher.2011Apr1;11(7):627-32.Epub2011Apr1.Review.PubMedPMID:21301207;PubMedCentralPMCID:PMC3084968.

2:ParveenN,CornellKA.Methylthioadenosine/S-adenosylhomocysteinenucleosidase,acriticalenzymeforbacterialmetabolism.MolMicrobiol.2011Jan;79(1):7-20.doi:10.1111/j.1365-2958.2010.07455.x.Epub2010Nov18.Review.PubMedPMID:21166890;PubMedCentralPMCID:PMC3057356.

3:AlbersE.Metaboliccharacteristicsandimportanceoftheuniversalmethioninesalvagepathwayrecyclingmethioninefrom5'-methylthioadenosine.IUBMBLife.2009Dec;61(12):1132-42.doi:10.1002/iub.278.Review.PubMedPMID:19946895.

4:AvilaMA,García-TrevijanoER,LuSC,CorralesFJ,MatoJM.Methylthioadenosine.IntJBiochemCellBiol.2004Nov;36(11):2125-30.Review.PubMedPMID:15313459.

5:DellaRagioneF,OlivaA,PalumboR,RussoGL,ZappiaV.Enzymedeficiencyandtumorsuppressorgenes:absenceof5'-deoxy-5'-methylthioadenosinephosphorylaseinhumantumors.AdvExpMedBiol.1993;348:31-43.Review.PubMedPMID:8172020.

6:DellaRagioneF,OlivaA,FiorettiM,RussoGL,PalumboR,ZappiaV.Physico-chemicalandimmunologicalpropertiesofbovineliver5'-deoxy-5'-methylthioadenosinephosphorylase.AdvExpMedBiol.1988;250:187-97.Review.PubMedPMID:3151226.

7:CarsonDA,NoboriT,KajanderEO,CarreraCJ,KubotaM,YamanakaH.Methylthioadenosine(MeSAdo)phosphorylasedeficiencyinmalignancy.AdvExpMedBiol.1988;250:179-85.Review.PubMedPMID:3151225.

8:ZappiaV,DellaRagioneF,PontoniG,GragnanielloV,Cartenì-FarinaM.Human5'-deoxy-5'-methylthioadenosinephosphorylase:kineticstudiesandcatalyticmechanism.AdvExpMedBiol.1988;250:165-77.Review.PubMedPMID:3151224.

9:SchlenkF.Methylthioadenosine.AdvEnzymolRelatAreasMolBiol.1983;54:195-265.Review.PubMedPMID:6405586.

10:Williams-AshmanHG,SeidenfeldJ,GallettiP.Trendsinthebiochemicalpharmacologyof5'-deoxy-5'-methylthioadenosine.BiochemPharmacol.1982Feb1;31(3):277-88.Review.PubMedPMID:6803807.