Synthesis and Antifungal Activity of Rhodopeptin Analogues. 1. Modification of the East and South Amino Acid Moieties

Structure−activity relationships of the east and south amino acid modified analogues of rhodopeptins, novel antifungal cyclic tetrapeptides isolated from Rhodococcus species Mer-N1033, have been investigated. It was observed that a basic amino acid moiety (lysine or ornithine) as the east amino acid...

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Bibliographic Details
Published in:Organic letters 2000-04, Vol.2 (7), p.973-976
Main Authors: Kawato, Haruko C, Nakayama, Kiyoshi, Inagaki, Hiroaki, Nakajima, Ryohei, Kitamura, Akihiro, Someya, Kazuhiko, Ohta, Toshiharu
Format: Article
Language:English
Subjects:
Amino Acids - chemistry
Antifungal Agents - chemical synthesis
Antifungal Agents - pharmacology
Fungi - drug effects
Microbial Sensitivity Tests
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - pharmacology
Rhodococcus - chemistry
Structure-Activity Relationship
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Summary:Structure−activity relationships of the east and south amino acid modified analogues of rhodopeptins, novel antifungal cyclic tetrapeptides isolated from Rhodococcus species Mer-N1033, have been investigated. It was observed that a basic amino acid moiety (lysine or ornithine) as the east amino acid and a hydrophobic and bulky neutral amino acid (i.e., γ-methylleucine) as the south amino acid were indispensable structure motifs for antifungal activity of rhodopeptin analogues.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol005631c