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Article: A New Strategy to Induce γ-Turns: Peptides Composed of Alternating α-Aminoxy Acids and α-Amino Acids

TitleA New Strategy to Induce γ-Turns: Peptides Composed of Alternating α-Aminoxy Acids and α-Amino Acids
Authors
Issue Date2003
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, 2003, v. 125 n. 43, p. 13018-13019 How to Cite?
AbstractIt is known that the seven-membered-ring intramolecular hydrogen bond (γ-turn) is seldom formed in naturally occurring peptides composed of α-amino acids. Here we report a new strategy to induce γ-turns in short linear peptides. We designed and synthesized several peptides (1-5) containing alternating α-L-aminoxy acids and α-D-amino acids. 1H NMR studies revealed that the γ-turn could be initiated by the following N-O turn, an eight-membered-ring intramolecular hydrogen bond induced by an α-aminoxy acid. Moreover, NOESY and CD studies suggested peptides 4 and 5 form a novel secondary structure, a mixed 7-8 helix. Theoretical calculations on several di-, tri-, and tetrapeptide models provided strong support to the above conclusions. Copyright © 2003 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/167842
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.authorLi, Wen_US
dc.contributor.authorQu, Jen_US
dc.contributor.authorLuo, SWen_US
dc.contributor.authorWu, YDen_US
dc.date.accessioned2012-10-08T03:12:07Z-
dc.date.available2012-10-08T03:12:07Z-
dc.date.issued2003en_US
dc.identifier.citationJournal Of The American Chemical Society, 2003, v. 125 n. 43, p. 13018-13019en_US
dc.identifier.issn0002-7863en_US
dc.identifier.urihttp://hdl.handle.net/10722/167842-
dc.description.abstractIt is known that the seven-membered-ring intramolecular hydrogen bond (γ-turn) is seldom formed in naturally occurring peptides composed of α-amino acids. Here we report a new strategy to induce γ-turns in short linear peptides. We designed and synthesized several peptides (1-5) containing alternating α-L-aminoxy acids and α-D-amino acids. 1H NMR studies revealed that the γ-turn could be initiated by the following N-O turn, an eight-membered-ring intramolecular hydrogen bond induced by an α-aminoxy acid. Moreover, NOESY and CD studies suggested peptides 4 and 5 form a novel secondary structure, a mixed 7-8 helix. Theoretical calculations on several di-, tri-, and tetrapeptide models provided strong support to the above conclusions. Copyright © 2003 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.meshAmides - Chemistryen_US
dc.subject.meshAmino Acids - Chemistryen_US
dc.subject.meshCircular Dichroismen_US
dc.subject.meshModels, Molecularen_US
dc.subject.meshNuclear Magnetic Resonance, Biomolecularen_US
dc.subject.meshPeptides - Chemistryen_US
dc.subject.meshProtein Conformationen_US
dc.subject.meshProtein Structure, Secondaryen_US
dc.titleA New Strategy to Induce γ-Turns: Peptides Composed of Alternating α-Aminoxy Acids and α-Amino Acidsen_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/ja036136pen_US
dc.identifier.pmid14570462-
dc.identifier.scopuseid_2-s2.0-0142245592en_US
dc.identifier.hkuros91777-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0142245592&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume125en_US
dc.identifier.issue43en_US
dc.identifier.spage13018en_US
dc.identifier.epage13019en_US
dc.identifier.isiWOS:000186123900016-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridYang, D=7404800756en_US
dc.identifier.scopusauthoridLi, W=36066858500en_US
dc.identifier.scopusauthoridQu, J=7201534485en_US
dc.identifier.scopusauthoridLuo, SW=35741176500en_US
dc.identifier.scopusauthoridWu, YD=7406892738en_US

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