Coprisamides A and B, New Branched Cyclic Peptides from a Gut Bacterium of the Dung Beetle Copris tripartitus

Coprisamides A and B, New Branched Cyclic Peptides from a Gut Bacterium of the Dung Beetle Copris tripartitus

Coprisamides A and B (1 and 2) were isolated from a bacterium in the gut of the dung beetle Copris tripartitus. Spectroscopic analysis revealed that the planar structures of 1 and 2 are novel cyclic heptapeptides bearing unusual units, such as β-methylaspartic acid and 2,3-diaminopropanoic acid bran...

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Veröffentlicht in:Organic letters 2015-03, Vol.17 (5), p.1272-1275
Hauptverfasser: Um, Soohyun, Park, So Hyun, Kim, Jihye, Park, Hyen Joo, Ko, Keebeom, Bang, Hea-Son, Lee, Sang Kook, Shin, Jongheon, Oh, Dong-Chan
Format: Artikel
Sprache:eng
Schlagworte:
Animals
Bacterial Physiological Phenomena - drug effects
beta-Alanine - analogs & derivatives
beta-Alanine - chemistry
Coleoptera - microbiology
Feces
Molecular Structure
Peptides, Cyclic - chemistry
Peptides, Cyclic - isolation & purification
Streptomyces - chemistry
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Zusammenfassung:Coprisamides A and B (1 and 2) were isolated from a bacterium in the gut of the dung beetle Copris tripartitus. Spectroscopic analysis revealed that the planar structures of 1 and 2 are novel cyclic heptapeptides bearing unusual units, such as β-methylaspartic acid and 2,3-diaminopropanoic acid branched to valine and 2-heptatrienyl cinnamic acid. Absolute configurations were established by chemical derivatization and chiroptical spectroscopy. The coprisamides displayed significant activity for induction of quinone reductase.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00249