Thioether sulfur oxygenation from O-2 or H2O2 reactivity of copper complexes with tridentate N2Sthioether ligands

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dc.contributor.authorLee, Yunhoko
dc.contributor.authorLee, DHko
dc.contributor.authorSarjeant, AANko
dc.contributor.authorZakharov, LNko
dc.contributor.authorRheingold, ALko
dc.contributor.authorKarlin, KDko
dc.date.accessioned2013-03-07T16:35:09Z-
dc.date.available2013-03-07T16:35:09Z-
dc.date.created2012-02-06-
dc.date.created2012-02-06-
dc.date.issued2006-12-
dc.identifier.citationINORGANIC CHEMISTRY, v.45, no.25, pp.10098 - 10107-
dc.identifier.issn0020-1669-
dc.identifier.urihttp://hdl.handle.net/10203/90689-
dc.description.abstractTo model thioether-copper coordination chemistry including oxidative reactivity, such as occurs in the copper monooxygenases peptidylglycine alpha-hydroxylating monooxygenase (PHM) and dopamine beta-hydroxylase (D beta H), we have synthesized new tridentate N2S ligands L-SEP and L-SBz [L-SEP = methyl(2-phenethylsulfanylpropyl)(2-pyridin-2-ylethyl) amine; LSBz) (2-benzylsulfanylpropyl)methyl(2-pyridin-2-ylethyl)amine)]. Both copper(I) and copper(II) complexes have been prepared, and their respective O-2 and H2O2 chemistry has been studied. Under mild conditions, oxygenation of [(L-SEP) Cu-I](+) (1a) and [(L-SBz)Cu-I](+) (2a) leads to ligand sulfoxidation, thus exhibiting copper monooxygenase activity. A copper(II) complex of this sulfoxide ligand product, [(L-SOEP)Cu-II(CH3OH)(OClO3)(2)], has been structurally characterized, demonstrating Cu-O-sulfoxide ligation. The X-ray structure of [(L-SEP)Cu-II(H2O)(OClO3)](+) (1b) and its solution UV-visible spectral properties [S-Cu-II LMCT band at 365 nm (MeCN solvent); epsilon = 4285 M-1 cm(-1)] indicate the thioether sulfur atom is bound to the cupric ion in both the solid (Cu-II-S distance: 2.31 angstrom) and solution states. Reaction of 1b with H2O2 leads to sulfonation via the sulfoxide; excess hydrogen peroxide gives mostly sulfone product. These results may provide some insight into recent reports concerning protein methionine oxidation, showing the potential importance of copper-mediated oxidation processes in certain biological settings.-
dc.languageEnglish-
dc.publisherAMER CHEMICAL SOC-
dc.subjectALPHA-HYDROXYLATING MONOOXYGENASE-
dc.subjectDOPAMINE BETA-MONOOXYGENASE-
dc.subjectMETHIONINE OXIDATION-
dc.subjectELECTRON-TRANSFER-
dc.subjectCATALYTIC MECHANISM-
dc.subjectDIOXYGEN-BINDING-
dc.subjectPEPTIDYLGLYCINE MONOOXYGENASE-
dc.subjectAROMATIC HYDROXYLATION-
dc.subjectPHYSICAL PARAMETERS-
dc.subjectTHIANTHRENE 5-OXIDE-
dc.titleThioether sulfur oxygenation from O-2 or H2O2 reactivity of copper complexes with tridentate N2Sthioether ligands-
dc.typeArticle-
dc.identifier.wosid000242479700027-
dc.identifier.scopusid2-s2.0-33846136924-
dc.type.rimsART-
dc.citation.volume45-
dc.citation.issue25-
dc.citation.beginningpage10098-
dc.citation.endingpage10107-
dc.citation.publicationnameINORGANIC CHEMISTRY-
dc.identifier.doi10.1021/ic060730t-
dc.contributor.localauthorLee, Yunho-
dc.contributor.nonIdAuthorLee, DH-
dc.contributor.nonIdAuthorSarjeant, AAN-
dc.contributor.nonIdAuthorZakharov, LN-
dc.contributor.nonIdAuthorRheingold, AL-
dc.contributor.nonIdAuthorKarlin, KD-
dc.type.journalArticleArticle-
dc.subject.keywordPlusALPHA-HYDROXYLATING MONOOXYGENASE-
dc.subject.keywordPlusDOPAMINE BETA-MONOOXYGENASE-
dc.subject.keywordPlusMETHIONINE OXIDATION-
dc.subject.keywordPlusELECTRON-TRANSFER-
dc.subject.keywordPlusCATALYTIC MECHANISM-
dc.subject.keywordPlusDIOXYGEN-BINDING-
dc.subject.keywordPlusPEPTIDYLGLYCINE MONOOXYGENASE-
dc.subject.keywordPlusAROMATIC HYDROXYLATION-
dc.subject.keywordPlusPHYSICAL PARAMETERS-
dc.subject.keywordPlusTHIANTHRENE 5-OXIDE-
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