Effect of hydrocarbon stapling on the properties of α-helical antimicrobial peptides isolated from the venom of hymenoptera
作者： Hubert Chapuis , Jiřina Slaninová , Lucie Bednárová , Lenka Monincová , Miloš Buděšínský
DOI: 10.1007/S00726-012-1283-1
关键词: Hydrocarbon 、 Antimicrobial peptides 、 Chemistry 、 Venom 、 α helical 、 Antimicrobial 、 Biochemistry 、 Alanine 、 Circular dichroism 、 Stereochemistry 、 Peptide
摘要: The impact of inserting hydrocarbon staples into short α-helical antimicrobial peptides lasioglossin III and melectin (antimicrobial wild bee venom) on their biological biophysical properties has been examined. stapling was achieved by ring-closing olefin metathesis, either between two S-2-(4′-pentenyl) alanine residues (S5) incorporated at i + 4 positions or R-2-(7′-octenyl) (R8) S5 the 7 positions, respectively. We prepared several analogs with a single staple inserted different within peptide chains as well double staples. stapled exhibited remarkable increase in hemolytic activity, while activities decreased. Some showed higher resistance against proteolytic degradation than native ones, were substantially more resistant. CD spectra singly measured water only slightly better propensity to form structure when compared peptides, whereas doubly dramatically enhanced α-helicity.
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