File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: β N-O turns and helices induced by β2-aminoxy peptides: Synthesis and conformational studies

Titleβ N-O turns and helices induced by β2-aminoxy peptides: Synthesis and conformational studies
Authors
Keywordsasymmetric synthesis
density functional calculations
hydrogen bonds
peptides
structure elucidation
Issue Date2011
PublisherWiley - V C H Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www.wiley-vch.de/publish/en/journals/alphabeticIndex/2451
Citation
Chemistry - An Asian Journal, 2011, v. 6 n. 7, p. 1791-1799 How to Cite?
AbstractHerein, we report an efficient route for the asymmetric synthesis of β 2-aminoxy acids as well as experimental and theoretical studies of conformations of peptides composed of β 2-aminoxy acids. The nine-membered-ring intramolecular hydrogen bonds, namely, β N-O turns, are generated between adjacent residues in those peptides, in accordance with our computational results. The presence of two consecutive homochiral β N-O turns leads to the formation of β N-O helical structures in solution, although both helical (composed of two β N-O turns of the same handedness) and reverse-turn (composed of two β N-O turns with opposite handedness) structures are of similar stability, as suggested by theoretical studies. Nevertheless, two slightly different conformations, with the same handedness, of β 2-aminoxy monomers have been observed in the solid state and in solution according to our X-ray and 2D NOESY studies. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Persistent Identifierhttp://hdl.handle.net/10722/139020
ISSN
2015 Impact Factor: 4.592
2015 SCImago Journal Rankings: 1.833
ISI Accession Number ID
Funding AgencyGrant Number
Fudan University
National Natural Science Foundation of China20202001
Fok Ying Tung Education Foundation94023
HKU-Fudan Joint Laboratory on Molecular Design and Synthesis
Research Grants Council of Hong KongHKU 7654/06M
Funding Information:

This work was supported by Fudan University, the National Natural Science Foundation of China (project no. 20202001), the Fok Ying Tung Education Foundation (project no. 94023), the HKU-Fudan Joint Laboratory on Molecular Design and Synthesis, and the Research Grants Council of Hong Kong (project no. HKU 7654/06M). D.-W.Z. would like to thank Fudan University for the conferment of the Century Star Award.

References
Grants

 

DC FieldValueLanguage
dc.contributor.authorJiao, ZGen_HK
dc.contributor.authorChang, XWen_HK
dc.contributor.authorDing, Wen_HK
dc.contributor.authorLiu, GJen_HK
dc.contributor.authorSong, KSen_HK
dc.contributor.authorZhu, NYen_HK
dc.contributor.authorZhang, DWen_HK
dc.contributor.authorYang, Den_HK
dc.date.accessioned2011-09-23T05:44:10Z-
dc.date.available2011-09-23T05:44:10Z-
dc.date.issued2011en_HK
dc.identifier.citationChemistry - An Asian Journal, 2011, v. 6 n. 7, p. 1791-1799en_HK
dc.identifier.issn1861-4728en_HK
dc.identifier.urihttp://hdl.handle.net/10722/139020-
dc.description.abstractHerein, we report an efficient route for the asymmetric synthesis of β 2-aminoxy acids as well as experimental and theoretical studies of conformations of peptides composed of β 2-aminoxy acids. The nine-membered-ring intramolecular hydrogen bonds, namely, β N-O turns, are generated between adjacent residues in those peptides, in accordance with our computational results. The presence of two consecutive homochiral β N-O turns leads to the formation of β N-O helical structures in solution, although both helical (composed of two β N-O turns of the same handedness) and reverse-turn (composed of two β N-O turns with opposite handedness) structures are of similar stability, as suggested by theoretical studies. Nevertheless, two slightly different conformations, with the same handedness, of β 2-aminoxy monomers have been observed in the solid state and in solution according to our X-ray and 2D NOESY studies. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.en_HK
dc.languageengen_US
dc.publisherWiley - V C H Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www.wiley-vch.de/publish/en/journals/alphabeticIndex/2451en_HK
dc.relation.ispartofChemistry - An Asian Journalen_HK
dc.subjectasymmetric synthesisen_HK
dc.subjectdensity functional calculationsen_HK
dc.subjecthydrogen bondsen_HK
dc.subjectpeptidesen_HK
dc.subjectstructure elucidationen_HK
dc.subject.meshHydrogen Bonding-
dc.subject.meshModels, Theoretical-
dc.subject.meshNitrogen - chemistry-
dc.subject.meshOxygen - chemistry-
dc.subject.meshPeptides - chemical synthesis - chemistry-
dc.titleβ N-O turns and helices induced by β2-aminoxy peptides: Synthesis and conformational studiesen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=1861-4728&volume=6&spage=1791&epage=1799&date=2011&atitle=β+N-O+turns+and+helices+induced+by+β2-aminoxy+peptides:+synthesis+and+conformational+studiesen_US
dc.identifier.emailZhu, NY: nzhu@hkucc.hku.hken_HK
dc.identifier.emailYang, D: yangdan@hku.hken_HK
dc.identifier.authorityZhu, NY=rp00845en_HK
dc.identifier.authorityYang, D=rp00825en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/asia.201000933en_HK
dc.identifier.pmid21523911en_US
dc.identifier.scopuseid_2-s2.0-79959955261en_HK
dc.identifier.hkuros196037en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-79959955261&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume6en_HK
dc.identifier.issue7en_HK
dc.identifier.spage1791en_HK
dc.identifier.epage1799en_HK
dc.identifier.isiWOS:000293135800018-
dc.publisher.placeGermanyen_HK
dc.relation.projectDeveloping aminoxy acids-containing peptide mimics as small moleucle inhibitors of protein-protein interactions-
dc.identifier.scopusauthoridJiao, ZG=54381988900en_HK
dc.identifier.scopusauthoridChang, XW=35319791100en_HK
dc.identifier.scopusauthoridDing, W=8249761400en_HK
dc.identifier.scopusauthoridLiu, GJ=7501460370en_HK
dc.identifier.scopusauthoridSong, KS=7401740599en_HK
dc.identifier.scopusauthoridZhu, NY=7201449530en_HK
dc.identifier.scopusauthoridZhang, DW=35320759400en_HK
dc.identifier.scopusauthoridYang, D=7404800756en_HK

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats