title: Substitution of the GalNAc-α-O-Thr¹¹ residue in drosocin with O-linked glyco-peptoid residue: effect on antibacterial activity and conformational change.
abstract: One of the obvious disadvantages of natural peptides is their liability to proteases. Among the several solutions for this issue, peptoids or oligomers of N-substituted glycine have emerged as a promising tool that may enhance the stability of proteolysis-susceptible natural peptides. We have synthesized the drosocin and its glyco-peptoid analogues linked O-GalNAc at the Thr(11) residue. One of our glyco-peptoid analogues showed an increased antibacterial activity by the modification of the Thr(11) residue with glyco-peptoid. Structure-activity relationship studies revealed that the antibacterial activity by glyco-peptoid drosocin requires three key elements: free hydroxyl group on the carbohydrate moiety, γ-methyl group of the Thr(11) residue derivative and (S)-configuration over (R)-configuration.
authors: Division of Magnetic Resonance, Korea Basic Science Institute, Ochang, Chung-Buk 363-883, Republic of Korea.
authors: Mija
authors: M
authors: Ahn
authors: Ravichandran N
authors: RN
authors: Murugan
authors: Yong Hai
authors: YH
authors: Nan
authors: Chaejoon
authors: C
authors: Cheong
authors: Hoik
authors: H
authors: Sohn
authors: Eun-Hee
authors: EH
authors: Kim
authors: Eunha
authors: E
authors: Hwang
authors: Eun Kyoung
authors: EK
authors: Ryu
authors: Shin Won
authors: SW
authors: Kang
authors: Song Yub
authors: SY
authors: Shin
authors: Jeong Kyu
authors: JK
authors: Bang
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology*; D023181:Antimicrobial Cationic Peptides / Q000737:chemistry / Q000494:pharmacology; D004331:Drosophila melanogaster / Q000737:chemistry*; D004926:Escherichia coli / Q000187:drug effects; D004927:Escherichia coli Infections / Q000188:drug therapy; D006020:Glycopeptides / Q000737:chemistry* / Q000494:pharmacology*; D019476:Insect Proteins / Q000737:chemistry / Q000494:pharmacology; D034444:Peptoids / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D023181:Antimicrobial Cationic Peptides; D006020:Glycopeptides; D019476:Insect Proteins; D034444:Peptoids; C082117:drosocin