Thiol-copper(I) and disulfide-dicopper(I) complex O-2-reactivity leading to sulfonate-copper(II) complex or the formation of a cross-linked thioether-phenol product with phenol addition

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dc.contributor.authorLee, Yunhoko
dc.contributor.authorLee, DHko
dc.contributor.authorSarjeant, AANko
dc.contributor.authorKarlin, KDko
dc.date.accessioned2013-03-07T16:08:07Z-
dc.date.available2013-03-07T16:08:07Z-
dc.date.created2012-02-06-
dc.date.created2012-02-06-
dc.date.issued2007-11-
dc.identifier.citationJOURNAL OF INORGANIC BIOCHEMISTRY, v.101, no.11-12, pp.1845 - 1858-
dc.identifier.issn0162-0134-
dc.identifier.urihttp://hdl.handle.net/10203/90641-
dc.description.abstractIn order to better understand copper mediated oxidative chemistry via ligand-Cu-1/O-2 reactivity employing S-donor ligands for copper, O-2-reactivity studies of the copper(I) complexes (1 and 2, Chart 2) have been carried out with a tridentate N2S thiol ligand (1-(N-methyl-N-(2-(pyridin-2-yl)ethyl)amino)propane-2-thiol; L-SH) or its oxidized disulfide form (L-ss). Reactions of [(LCu1)-Cu-SH](+) (1) and [L-ss(CU1)(2)(X)(2)](2+) (2) with O-2 give similar to 90% and similar to 70% yields of [(LCuII)-Cu-SO3(MeOH)(2)](+) (3), respectively, where L-SO3 is S-oxygenated sulfonate; 3 was characterized by electrospray ionization (ESI) mass spectrometry and X-ray crystallography. Mimicking TyrCys galactose oxidase cofactor biogenesis, a new C-S bond is formed (within new thioether moiety L-SPhOH) from cuprous complex (both I and 2) dioxygen reactivity in the presence of 2,4-tBu(2)-phenolate. In addition, the disulfide ligand (L-SS) reacts with 2 equiv. cupric ion salts and the phenolate to efficiently give the cross-linked product L-SPhOH in high yield (>90%) under anaerobic conditions. Separately, complex [(LCuII)-Cu-SPhO(ClO4)] (4), possessing the cross-linked L-SPhOH, was characterized by ESI mass spectrometry and X-ray crystallography. (c) 2007 Elsevier Inc. All rights reserved.-
dc.languageEnglish-
dc.publisherELSEVIER SCIENCE INC-
dc.subjectDISULFIDE-BRIDGED DICOPPER(I)-
dc.subjectCYTOCHROME-C-OXIDASE-
dc.subjectCONTROLLED OXIDATIVE POLYMERIZATION-
dc.subjectPROTEIN-SULFENIC ACIDS-
dc.subjectSULFUR DONOR LIGANDS-
dc.subjectBLUE COPPER PROTEINS-
dc.subjectCRYSTAL-STRUCTURE-
dc.subjectCYSTEINE DIOXYGENASE-
dc.subjectGALACTOSE-OXIDASE-
dc.subjectNITRILE HYDRATASE-
dc.titleThiol-copper(I) and disulfide-dicopper(I) complex O-2-reactivity leading to sulfonate-copper(II) complex or the formation of a cross-linked thioether-phenol product with phenol addition-
dc.typeArticle-
dc.identifier.wosid000251523100037-
dc.identifier.scopusid2-s2.0-35348825585-
dc.type.rimsART-
dc.citation.volume101-
dc.citation.issue11-12-
dc.citation.beginningpage1845-
dc.citation.endingpage1858-
dc.citation.publicationnameJOURNAL OF INORGANIC BIOCHEMISTRY-
dc.identifier.doi10.1016/j.jinorgbio.2007.06.016-
dc.contributor.localauthorLee, Yunho-
dc.contributor.nonIdAuthorLee, DH-
dc.contributor.nonIdAuthorSarjeant, AAN-
dc.contributor.nonIdAuthorKarlin, KD-
dc.type.journalArticleArticle-
dc.subject.keywordAuthorcopper complexes-
dc.subject.keywordAuthorcopper-O-2 chemistry-
dc.subject.keywordAuthorsulfonate formation-
dc.subject.keywordAuthorsulfur-phenol cross-link-
dc.subject.keywordAuthorcrystal structures-
dc.subject.keywordPlusDISULFIDE-BRIDGED DICOPPER(I)-
dc.subject.keywordPlusCYTOCHROME-C-OXIDASE-
dc.subject.keywordPlusCONTROLLED OXIDATIVE POLYMERIZATION-
dc.subject.keywordPlusPROTEIN-SULFENIC ACIDS-
dc.subject.keywordPlusSULFUR DONOR LIGANDS-
dc.subject.keywordPlusBLUE COPPER PROTEINS-
dc.subject.keywordPlusCRYSTAL-STRUCTURE-
dc.subject.keywordPlusCYSTEINE DIOXYGENASE-
dc.subject.keywordPlusGALACTOSE-OXIDASE-
dc.subject.keywordPlusNITRILE HYDRATASE-
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