title: Structure activity relationship study of burkholdine analogues toward simple antifungal agents.
abstract: Cyclic and linear lipopeptides, burkholdine analogues, were synthesized by conventional Fmoc-SPPS and cyclisation with DIPC/HOBt in the solution phase. Synthesized peptides were evaluated for antifungal activities with MIC values against Saccharomyces cerevisiae and Aspergillus oryzae. As a result, the stereochemistry of the amino acid residues and sequences of burkholdine analogues exerted a significant influence on antifungal activities. In addition, we found a linear burkholdine analogue with moderate antifungal activities.
authors.affiliation: Department of Biological Engineering, Graduate School of Science and Technology, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan. Electronic address: konno@yz.yamagata-u.ac.jp.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Konno
authors.affiliation: Department of Biological Engineering, Graduate School of Science and Technology, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan.
authors.forename: Kanako
authors.initials: K
authors.lastname: Abumi
authors.affiliation: Department of Biological Engineering, Graduate School of Science and Technology, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan.
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Sasaki
authors.affiliation: Department of Biological Engineering, Graduate School of Science and Technology, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan.
authors.forename: Shigekazu
authors.initials: S
authors.lastname: Yano
authors.affiliation: School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women's University, 9-11-68 Koshien, Nishinomiya, Hyogo 663-8179, Japan.
authors.forename: Kazuto
authors.initials: K
authors.lastname: Nosaka
mesh_terms: D000596:Amino Acids / Q000032:analysis; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001236:Aspergillus oryzae / Q000187:drug effects; D019117:Burkholderia / Q000737:chemistry; D002175:Candida / Q000187:drug effects; D003500:Cyclization; D015195:Drug Design; D055666:Lipopeptides / Q000737:chemistry* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D009842:Oligopeptides / Q000138:chemical synthesis / Q000494:pharmacology; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000494:pharmacology*; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000596:Amino Acids; D000935:Antifungal Agents; D055666:Lipopeptides; D009842:Oligopeptides; D010456:Peptides, Cyclic; C000718065:burkholdine
keywords: Antifungal; Burkholdine; Lipopeptide; Structure activity relationship study