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
作者： Rajesh Sonti , Konkallu Hanumae Gowd , K. N. Shashanka Rao , Srinivasarao Ragothama , Alex Rodriguez
关键词: Chemistry 、 Chemical shift 、 Isomerization 、 Poison control 、 Peptide 、 Stereochemistry 、 Conus 、 Cyclic peptide 、 Ring (chemistry) 、 Cis–trans isomerism
摘要: Conformational diversity or shapeshifting in cyclic peptide natural products can, principle, confer a single molecular entity with the property of binding to multiple receptors. equilibria have been probed contryphans, which are peptides derived from Conus venom possessing 23-membered disulfide moiety. The sequences inscriptus, GCV(D)LYPWC* (In936) and loroisii, GCP(D)WDPWC* (Lo959) differ number proline residues within macrocyclic ring. Structural characterisation distinct conformational states arising cis-trans about Xxx-Pro bonds is reported. Isomerisation C2-P3 bond observed case Lo959 Y5-P6 In936. Evidence presented for as many four species synthetic analogue V3P Tyr-Pro-Trp segment In936 characterised by sidechain orientations consequence aromatic/proline interactions evidenced specific sidechain-sidechain nuclear Overhauser effects ring current shifted proton chemical shifts. Molecular dynamics simulations suggest that Tyr5 Trp7 conformations correlated depend on geometry bond. Thermodynamic parameters cis trans equilibrium Studies analogues provide insights into role sequence modulating isomerisation bonds.
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