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Article: Macrocyclic effect of auxiliary ligand on the gas-phase dissociation of ternary copper(II)-GGX complexes

TitleMacrocyclic effect of auxiliary ligand on the gas-phase dissociation of ternary copper(II)-GGX complexes
Authors
Issue Date2006
PublisherJohn Wiley & Sons Ltd. The Journal's web site is located at http://www.interscience.wiley.com/jpages/0951-4198/
Citation
Rapid Communications In Mass Spectrometry, 2006, v. 20 n. 5, p. 790-796 How to Cite?
AbstractPrevious studies into the dissociation of [Cu II(dien)peptide] .2+ ions (dien = diethylenetriamine) have shown that NH-containing auxiliary ligands do not favor the formation of [peptide] .+ species; instead, they promote proton-transfer reactions, especially for peptides containing basic amino residues. Formation of radical cationic tripeptides of the form GGX .+ [GGX = glycylglycyl(residue X)] becomes feasible upon substituting the open-chain tridentate ligand dien with its analogous cyclic ligand, 1,4,7-triazacyclononane (9-aneN 3); i.e., from [Cu II(9-aneN 3)GGX] .2+ ions. Similar enhancements occur when using 1,4,7,10-tetraoxacyclododecane (12-crown-4) in place of its open-chain analog, 2,5,8,11-tetraoxadecane (triglyme). We have demonstrated that a sterically encumbered auxiliary macrocyclic ligand within [Cu II(L)GGX] .2+ complex ions [where L = 9-aneN 3 or 12-crown-4] facilitates the formation of radical cationic peptides through gas-phase fragmentation. We verified our experimental observations by examining the reactivities of a series of 19 tripeptides of the type GGX that differ only in the identity of their C-terminal residue. The energy of the electron-transfer reaction correlates well with the bond-dissociation energy of the peptide-Cu(II) interaction; the presence of a constrained macrocyclic ligand weakens metal-peptide chelation through steric repulsion between the ligand and the peptide, and this situation may lead to more favorable radical cationic peptide formation. Copyright © 2006 John Wiley & Sons, Ltd.
Persistent Identifierhttp://hdl.handle.net/10722/70063
ISSN
2015 Impact Factor: 2.226
2015 SCImago Journal Rankings: 0.819
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorLam, CNWen_HK
dc.contributor.authorSiu, SOen_HK
dc.contributor.authorOrlova, Gen_HK
dc.contributor.authorChu, IKen_HK
dc.date.accessioned2010-09-06T06:19:22Z-
dc.date.available2010-09-06T06:19:22Z-
dc.date.issued2006en_HK
dc.identifier.citationRapid Communications In Mass Spectrometry, 2006, v. 20 n. 5, p. 790-796en_HK
dc.identifier.issn0951-4198en_HK
dc.identifier.urihttp://hdl.handle.net/10722/70063-
dc.description.abstractPrevious studies into the dissociation of [Cu II(dien)peptide] .2+ ions (dien = diethylenetriamine) have shown that NH-containing auxiliary ligands do not favor the formation of [peptide] .+ species; instead, they promote proton-transfer reactions, especially for peptides containing basic amino residues. Formation of radical cationic tripeptides of the form GGX .+ [GGX = glycylglycyl(residue X)] becomes feasible upon substituting the open-chain tridentate ligand dien with its analogous cyclic ligand, 1,4,7-triazacyclononane (9-aneN 3); i.e., from [Cu II(9-aneN 3)GGX] .2+ ions. Similar enhancements occur when using 1,4,7,10-tetraoxacyclododecane (12-crown-4) in place of its open-chain analog, 2,5,8,11-tetraoxadecane (triglyme). We have demonstrated that a sterically encumbered auxiliary macrocyclic ligand within [Cu II(L)GGX] .2+ complex ions [where L = 9-aneN 3 or 12-crown-4] facilitates the formation of radical cationic peptides through gas-phase fragmentation. We verified our experimental observations by examining the reactivities of a series of 19 tripeptides of the type GGX that differ only in the identity of their C-terminal residue. The energy of the electron-transfer reaction correlates well with the bond-dissociation energy of the peptide-Cu(II) interaction; the presence of a constrained macrocyclic ligand weakens metal-peptide chelation through steric repulsion between the ligand and the peptide, and this situation may lead to more favorable radical cationic peptide formation. Copyright © 2006 John Wiley & Sons, Ltd.en_HK
dc.languageengen_HK
dc.publisherJohn Wiley & Sons Ltd. The Journal's web site is located at http://www.interscience.wiley.com/jpages/0951-4198/en_HK
dc.relation.ispartofRapid Communications in Mass Spectrometryen_HK
dc.rightsRapid Communications in Mass Spectrometry. Copyright © John Wiley & Sons Ltd.en_HK
dc.titleMacrocyclic effect of auxiliary ligand on the gas-phase dissociation of ternary copper(II)-GGX complexesen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0951-4198&volume=20&spage=790&epage=796&date=2006&atitle=Macrocyclic+effect+of+auxiliary+ligand+on+the+gas+phase+dissociation+of+ternary+copper(II)–GGX+complexesen_HK
dc.identifier.emailChu, IK:ivankchu@hku.hken_HK
dc.identifier.authorityChu, IK=rp00683en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/rcm.2366en_HK
dc.identifier.scopuseid_2-s2.0-33644652134en_HK
dc.identifier.hkuros113869en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-33644652134&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume20en_HK
dc.identifier.issue5en_HK
dc.identifier.spage790en_HK
dc.identifier.epage796en_HK
dc.identifier.isiWOS:000235755000010-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridLam, CNW=36799179600en_HK
dc.identifier.scopusauthoridSiu, SO=8603087200en_HK
dc.identifier.scopusauthoridOrlova, G=7007153895en_HK
dc.identifier.scopusauthoridChu, IK=7103327484en_HK

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