Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
Rice, L. B. The clinical consequences of antimicrobial resistance. Curr. Opin. Microbiol. 12, 476–481 (2009).
Cai, J. C. et al. Linezolid-resistant clinical isolates of meticillin-resistant coagulase-negative staphylococci and Enterococcus faecium from China. J. Med. Microbiol. 61, 1568–1573 (2012).
Sawa, R. et al. Amycolamicin: a novel broad-spectrum antibiotic inhibiting bacterial topoisomerase. Chem. Eur. J. 18, 15772–15781 (2012).
Hashizume, H. et al. Tripropeptins, novel antimicrobial agents produced by Lysobacter sp. I. Taxonomy, isolation and biological activities. J. Antibiot. 54, 1054–1059 (2001).
Hashizume, H. et al. Tripropeptins, novel antimicrobial agents produced by Lysobacter sp. II. Structure elucidation. J. Antibiot. 57, 52–58 (2004).
Hashizume, H., Hattori, S., Igarashi, M. & Akamatsu, Y. Tripropeptin E, a new tripropeptin group antibiotic produced by Lysobacter sp. BMK333-48F3. J. Antibiot. 57, 394–399 (2004).
Hashizume, H. et al Tripropeptin C blocks lipid cycle of peptidoglycan synthesis by complex formation with undecaprenyl pyrophosphate. 50th Interscience Conference on Antimicrobial Agents and Chemotherapy, Boston, Poster F-1611 (2010).
Shoji, J. et al. Isolation and characterization of new peptide antibiotics, plusbacins A1-A4 and B1-B4. J. Antibiot. 45, 817–823 (1992).
Shoji, J. et al. Structure of new peptide antibiotics, plusbacins A1-A4 and B1-B4. J. Antibiot. 45, 824–831 (1992).
Konishi, M. et al. Empedopeptin (BMY-28117), a new depsipeptide antibiotic. I. Production, isolation and properties. J. Antibiot. 37, 949–957 (1984).
Sugawara, K., Numata, K., Konishi, M. & Kawaguchi, H. Empedopeptin (BMY-28117), a new depsipeptide antibiotic. II. Structure determination. J. Antibiot. 37, 958–964 (1984).
Hashizume, H. et al. Tripropeptin C blocks the lipid cycle of cell wall biosynthesis by complex formation with undecaprenyl pyrophosphate. Antimicrob. Agents Chemother. 55, 3821–3828 (2011).
Aboderin, A. A., Delpierre, G. R. & Fruton, J. S. Benzhydryl esters of amino acids in peptide synthesis. J. Am. Chem. Soc. 87, 5469–5472 (1965).
Murakami, M., Itou, Y., Isida, K. & Shin, H. J. Prenylagaramides A and B, new cyclic peptides from two strains of Oscillatoria agardhii. J. Natl Prod. 62, 752–755 (1999).
Acknowledgements
We greatly appreciate the assistance of Dr Yoshihiko Kobayashi of the Institute of Microbial Chemistry (BIKAKEN), Hiyoshi, for constructive discussions. We are also grateful to Kunio Inoue of the Institute of Microbial Chemistry (BIKAKEN), Tokyo, for determining the spectra of the antibacterial compounds and Dr Ryuichi Sawa of the Institute of Microbial Chemistry (BIKAKEN), Tokyo, for the MS experiments.
Author information
Authors and Affiliations
Corresponding author
Additional information
Supplementary Information accompanies the paper on The Journal of Antibiotics website
Supplementary information
Rights and permissions
About this article
Cite this article
Hirosawa, S., Takahashi, Y., Hashizume, H. et al. Synthesis and antibacterial activity of tripropeptin C derivatives modified at the carboxyl groups. J Antibiot 67, 265–268 (2014). https://doi.org/10.1038/ja.2013.128
Received:
Revised:
Accepted:
Published:
Issue date:
DOI: https://doi.org/10.1038/ja.2013.128
Keywords
This article is cited by
-
Precursor-directed biosynthesis and biological activity of tripropeptin Cpip, a new tripropeptin C analog containing pipecolic acid
The Journal of Antibiotics (2024)
-
In vivo efficacy of β-lactam/tripropeptin C in a mouse septicemia model and the mechanism of reverse β-lactam resistance in methicillin-resistant Staphylococcus aureus mediated by tripropeptin C
The Journal of Antibiotics (2018)
-
Natural lipopeptide antibiotic tripropeptin C revitalizes and synergistically potentiates the activity of beta-lactams against methicillin-resistant Staphylococcus aureus
The Journal of Antibiotics (2015)