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Article: Synthesis and conformational studies of γ-aminoxy peptides

TitleSynthesis and conformational studies of γ-aminoxy peptides
Authors
Issue Date2008
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, 2008, v. 130 n. 2, p. 743-755 How to Cite?
AbstractWe have synthesized a series of γ-aminoxy acids, including unsubstituted and γ4-Ph-, γ4-alkyl-, and γ3,4-cyclohexyl-substituted systems. Coupling of these monomers to oligomers can be realized using EDCl/HOBt (or HOAt) as the coupling agent. γ-Aminoxy peptides can form 10-membered-ring intramolecular hydrogen bonds - so-called "γ N-O turns" - between adjacent residues, the extent of which is controlled by the nature of the side chain of each γ-aminoxy acid residue, increasing from the unsubstituted γ-aminoxy peptide to the γ4-alkyl aminoxy peptides to the γ4-phenyl- and γ3,4-cyclohexyl-substituted aminoxy peptides. The presence of two consecutive homochiral 10-membered-ring intramolecular hydrogen bonds leads to the formation of a novel helical structure. Theoretical studies on a series of model peptides rationalize very well the experimentally observed conformational features of these γ-aminoxy peptides. © 2008 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/168278
ISSN
2015 Impact Factor: 13.038
2015 SCImago Journal Rankings: 7.123
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorChen, Fen_US
dc.contributor.authorSong, KSen_US
dc.contributor.authorWu, YDen_US
dc.contributor.authorYang, Den_US
dc.date.accessioned2012-10-08T03:16:57Z-
dc.date.available2012-10-08T03:16:57Z-
dc.date.issued2008en_US
dc.identifier.citationJournal Of The American Chemical Society, 2008, v. 130 n. 2, p. 743-755en_US
dc.identifier.issn0002-7863en_US
dc.identifier.urihttp://hdl.handle.net/10722/168278-
dc.description.abstractWe have synthesized a series of γ-aminoxy acids, including unsubstituted and γ4-Ph-, γ4-alkyl-, and γ3,4-cyclohexyl-substituted systems. Coupling of these monomers to oligomers can be realized using EDCl/HOBt (or HOAt) as the coupling agent. γ-Aminoxy peptides can form 10-membered-ring intramolecular hydrogen bonds - so-called "γ N-O turns" - between adjacent residues, the extent of which is controlled by the nature of the side chain of each γ-aminoxy acid residue, increasing from the unsubstituted γ-aminoxy peptide to the γ4-alkyl aminoxy peptides to the γ4-phenyl- and γ3,4-cyclohexyl-substituted aminoxy peptides. The presence of two consecutive homochiral 10-membered-ring intramolecular hydrogen bonds leads to the formation of a novel helical structure. Theoretical studies on a series of model peptides rationalize very well the experimentally observed conformational features of these γ-aminoxy peptides. © 2008 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.meshCircular Dichroismen_US
dc.subject.meshHydrogen Bondingen_US
dc.subject.meshOligopeptides - Chemical Synthesis - Chemistryen_US
dc.subject.meshProtein Structure, Secondaryen_US
dc.subject.meshSpectrophotometry, Infrareden_US
dc.titleSynthesis and conformational studies of γ-aminoxy peptidesen_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/ja0772750en_US
dc.identifier.pmid18088122-
dc.identifier.scopuseid_2-s2.0-40149088073en_US
dc.identifier.hkuros151121-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-40149088073&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume130en_US
dc.identifier.issue2en_US
dc.identifier.spage743en_US
dc.identifier.epage755en_US
dc.identifier.isiWOS:000252292500070-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridChen, F=7404908085en_US
dc.identifier.scopusauthoridSong, KS=7401740599en_US
dc.identifier.scopusauthoridWu, YD=7406892738en_US
dc.identifier.scopusauthoridYang, D=7404800756en_US

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