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Article: Cyclic hexapeptide of D,L-α-aminoxy acids as a selective receptor for chloride ion

TitleCyclic hexapeptide of D,L-α-aminoxy acids as a selective receptor for chloride ion
Authors
Issue Date2002
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html
Citation
Journal Of The American Chemical Society, 2002, v. 124 n. 42, p. 12410-12411 How to Cite?
AbstractCyclic hexapeptide 2, prepared from linear hexapeptide 1 of alternating D- and L-α-aminoxy acids, was found to adopt a C 3 symmetric and bracelet-like conformation with consecutive eight-membered-ring hydrogen bonds (N-O turns) in nonpolar solvents, similar to that of valinomycin, a cyclodepsipeptide that binds cations selectively. However, 2 showed affinities for halide ions with selectivity following the order of Cl - ≫ F - ≫ Br -. The observed higher selectivity for Cl - (K a = 11880 M -1) over F - (K a = 30 M -1) in CD 2Cl 2 suggested that the selectivity of 2 for halide ions is mainly governed by the size complementarity rather than the hydrogen-bonding strength. Upon Cl - ion binding, the original bracelet-like conformation of 2 turned into a rather flat conformation with all six amide NHs pointing inward to form hydrogen bonds with Cl -. Copyright © 2002 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/167766
ISSN
2015 Impact Factor: 13.038
2015 SCImago Journal Rankings: 7.123
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorYang, Den_US
dc.contributor.authorQu, Jen_US
dc.contributor.authorLi, Wen_US
dc.contributor.authorZhang, YHen_US
dc.contributor.authorRen, Yen_US
dc.contributor.authorWang, DPen_US
dc.contributor.authorWu, YDen_US
dc.date.accessioned2012-10-08T03:11:19Z-
dc.date.available2012-10-08T03:11:19Z-
dc.date.issued2002en_US
dc.identifier.citationJournal Of The American Chemical Society, 2002, v. 124 n. 42, p. 12410-12411en_US
dc.identifier.issn0002-7863en_US
dc.identifier.urihttp://hdl.handle.net/10722/167766-
dc.description.abstractCyclic hexapeptide 2, prepared from linear hexapeptide 1 of alternating D- and L-α-aminoxy acids, was found to adopt a C 3 symmetric and bracelet-like conformation with consecutive eight-membered-ring hydrogen bonds (N-O turns) in nonpolar solvents, similar to that of valinomycin, a cyclodepsipeptide that binds cations selectively. However, 2 showed affinities for halide ions with selectivity following the order of Cl - ≫ F - ≫ Br -. The observed higher selectivity for Cl - (K a = 11880 M -1) over F - (K a = 30 M -1) in CD 2Cl 2 suggested that the selectivity of 2 for halide ions is mainly governed by the size complementarity rather than the hydrogen-bonding strength. Upon Cl - ion binding, the original bracelet-like conformation of 2 turned into a rather flat conformation with all six amide NHs pointing inward to form hydrogen bonds with Cl -. Copyright © 2002 American Chemical Society.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.htmlen_US
dc.relation.ispartofJournal of the American Chemical Societyen_US
dc.subject.meshAmino Acids - Chemistryen_US
dc.subject.meshChloride Channels - Chemistry - Metabolismen_US
dc.subject.meshChlorides - Chemistry - Metabolismen_US
dc.subject.meshKineticsen_US
dc.subject.meshModels, Molecularen_US
dc.subject.meshNuclear Magnetic Resonance, Biomolecularen_US
dc.subject.meshOligopeptides - Chemical Synthesis - Chemistry - Pharmacologyen_US
dc.subject.meshPeptides, Cyclic - Chemical Synthesis - Chemistry - Metabolismen_US
dc.subject.meshProtein Conformationen_US
dc.titleCyclic hexapeptide of D,L-α-aminoxy acids as a selective receptor for chloride ionen_US
dc.typeArticleen_US
dc.identifier.emailYang, D:yangdan@hku.hken_US
dc.identifier.authorityYang, D=rp00825en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/ja027073yen_US
dc.identifier.pmid12381172-
dc.identifier.scopuseid_2-s2.0-0037163996en_US
dc.identifier.hkuros75914-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0037163996&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume124en_US
dc.identifier.issue42en_US
dc.identifier.spage12410en_US
dc.identifier.epage12411en_US
dc.identifier.isiWOS:000178672900009-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridYang, D=7404800756en_US
dc.identifier.scopusauthoridQu, J=7201534485en_US
dc.identifier.scopusauthoridLi, W=36066858500en_US
dc.identifier.scopusauthoridZhang, YH=8379010100en_US
dc.identifier.scopusauthoridRen, Y=7403274496en_US
dc.identifier.scopusauthoridWang, DP=7407069947en_US
dc.identifier.scopusauthoridWu, YD=7406892738en_US

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