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Conformational diversity in contryphans from conus venom: Cis-trans isomerisation and aromatic/proline interactions in the 23-membered ring of a 7-residue peptide disulfide loop

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10.1002/chem.201301722
 
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hdl:2117/21326

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Sonti, Rajesh
Gowd, Konkallu Hanumae
Rao, K. N Shashanka
Ragothama, Srinivasarao
Rodríguez García, Alejandro
Pérez González, Juan JesúsMés informacióMés informacióMés informació
Balaram, Padmanabhan
Document typeArticle
Defense date2013-11-05
Rights accessRestricted access - publisher's policy
Attribution-NonCommercial-NoDerivs 3.0 Spain
Except where otherwise noted, content on this work is licensed under a Creative Commons license : Attribution-NonCommercial-NoDerivs 3.0 Spain
Abstract
Conformational diversity or “shapeshifting” in cyclic peptide natu- ral products can, in principle, confer a single molecular entity with the proper- ty of binding to multiple receptors. Conformational equilibria have been probed in the contryphans, which are peptides derived from Conus venom possessing a 23-membered cyclic disul- fide moiety. The natural sequences derived from Conus inscriptus , GCV D LYPWC* (In936) and Conus lor- oisii , GCP D WDPWC* (Lo959) differ in the number of proline residues within the macrocyclic ring. Structural charac- terisation of distinct conformational states arising from cis – trans equilibria about Xxx–Pro bonds is reported. Iso- merisation about the C2–P3 bond is observed in the case of Lo959 and about the Y5–P6 bond in In936. Evi- dence is presented for as many as four distinct species in the case of the syn- thetic analogue V3P In936. The Tyr- Pro-Trp segment in In936 is character- ised by distinct sidechain orientations as a consequence of aromatic/proline interactions as evidenced by specific sidechain–sidechain nuclear Overhaus- er effects and ring current shifted proton chemical shifts. Molecular dy- namics simulations suggest that Tyr5 and Trp7 sidechain conformations are correlated and depend on the geometry of the Xxx–Pro bond. Thermodynamic parameters are derived for the cis $ trans equilibrium for In936. Studies on synthetic analogues provide insights into the role of sequence effects in modulating isomerisation about Xxx– Pro bonds.
CitationSonti, R. [et al.]. Conformational diversity in contryphans from conus venom: Cis-trans isomerisation and aromatic/proline interactions in the 23-membered ring of a 7-residue peptide disulfide loop. "Chemistry: a european journal", 05 Novembre 2013, vol. 19, núm. 45, p. 15175-15189. 
URIhttp://hdl.handle.net/2117/21326
DOI10.1002/chem.201301722
ISSN0947-6539
Publisher versionhttp://onlinelibrary.wiley.com/doi/10.1002/chem.201301722/abstract;jsessionid=096D99BBFD47ABB70EBAE9F31F5179AB.f04t03
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