Precursor‐Directed Diversification of Cyclic Tetrapeptidic Pseudoxylallemycins

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...

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Published inChembiochem : a European journal of chemical biology Vol. 19; no. 21; pp. 2307 - 2311
Main Authors Guo, Huijuan, Schmidt, Alexander, Stephan, Philipp, Raguž, Luka, Braga, Daniel, Kaiser, Marcel, Dahse, Hans‐Martin, Weigel, Christiane, Lackner, Gerald, Beemelmanns, Christine
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 02.11.2018
Wiley Subscription Services, Inc
Subjects
allenes
Amino acids
Antimicrobial activity
bioactivity
Biochemistry & Molecular Biology
Biological activity
Chemistry, Medicinal
Clinical trials
Drug development
Life Sciences & Biomedicine
Medical research
natural products
Peptides
Pharmacology & Pharmacy
Precursors
Pseudomonas aeruginosa
Science & Technology
synthases
Tyrosine
METABOLITES
XYLARIA
NONRIBOSOMAL PEPTIDE SYNTHETASES
NATURAL-PRODUCTS
amino acids
MACHINERY
peptides
LOGIC
synthases
allenes
natural products
ASSEMBLY LINES
bioactivity
BIOSYNTHESIS
POLYKETIDE
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Summary: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. Pep talk: 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. Herein, 21 new cyclic pseudoxylallemycin tetrapeptides are identified; their antimicrobial activities are assessed, and first studies towards their chemical derivatization are performed.
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ISSN:1439-4227
1439-7633
DOI:10.1002/cbic.201800503