title: Synthesis and antifungal activities of cyclic octa-lipopeptide burkholdine analogues.
abstract: Synthesis and antifungal activity of cyclic octapeptide derivatives of burkholdines are described. To construct cyclic octapeptides, the combination of Fmoc-SPPS and cyclization with DIC/HOBt in the solution phase was employed. Synthesized peptides were evaluated for antifungal activity with MIC values against Saccharomyces cerevisiae, Aspergillus oryzae, and Candida viswanathii. As a result, the lipid side chain and the stereochemistry of each amino acid of Bk-1097 analogues significantly affected antifungal activity.
authors.affiliation: Department of Biological Engineering, Graduate School of Science and Technology, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan. konno@yz.yamagata-u.ac.jp
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Konno
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Otsuki
authors.forename: Kenta
authors.initials: K
authors.lastname: Matsuzaki
authors.forename: Kazuto
authors.initials: K
authors.lastname: Nosaka
mesh_terms: D000595:Amino Acid Sequence; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001236:Aspergillus oryzae / Q000187:drug effects; D002175:Candida / Q000187:drug effects; D055666:Lipopeptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D055666:Lipopeptides; D010456:Peptides, Cyclic; C000718065:burkholdine