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Precursor‐Directed Diversification of Cyclic Tetrapeptidic Pseudoxylallemycins
Author(s) -
Guo Huijuan,
Schmidt Alexander,
Stephan Philipp,
Raguž Luka,
Braga Daniel,
Kaiser Marcel,
Dahse HansMartin,
Weigel Christiane,
Lackner Gerald,
Beemelmanns Christine
Publication year - 2018
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201800503
Subject(s) - moiety , cyclic peptide , antimicrobial , tyrosine , broad spectrum , amino acid , pseudomonas aeruginosa , chemistry , stereochemistry , drug discovery , combinatorial chemistry , diversification (marketing strategy) , biochemistry , bacteria , computational biology , biology , peptide , organic chemistry , genetics , marketing , business
Cyclic peptides containing non‐proteinogenic amino acids often exhibit a broad bioactivity spectrum and many have entered clinical trials with good prospects for drug development. We recently reported the discovery of six cyclic tetrapeptides, pseudoxylallemycins A–F ( 1 – 6 ), from a termite‐associated Pseudoxylaria sp. X802. These compounds contain a rare O ‐homoallenyl‐ l ‐tyrosine moiety and show promising antimicrobial activity against the Gram‐negative pathogenic bacterium Pseudomonas aeruginosa . To perform more detailed structure–activity studies, we pursued a precursor‐directed diversification strategy. Herein, we report the purification, identification, and testing of 21 new pseudoxylallemycin derivatives.