Synthesis and antibacterial activity of tripropeptin C derivatives modified at the carboxyl groups

Journal of Antibiotics

Volumn 67, Issue 3, 2014, Pages 265-268

  Hirosawa, Sehei ^a   Takahashi, Yoshiaki ^a   Hashizume, Hideki ^b   Miyake, Toshiaki ^a   Akamatsu, Yuzuru ^b  

^a Institute of Microbial Chemistry (BIKAKEN) Hiyoshi   (Japan)

^b INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

Author keywords

Antibacterial activity; MRSA; Synthesis; Tripropeptin

Indexed keywords

ANTIINFECTIVE AGENT; ASPARTIC ACID; CARBOXYL GROUP; CARBOXYLIC ACID; ESTER; HYDROXYL GROUP; LACTONE; TRIFLUOROACETIC ACID; TRIPROPEPTIN C; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; ESTERIFICATION; FOLLOW UP; HETERONUCLEAR MULTIPLE BOND CORRELATION; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; METHICILLIN SUSCEPTIBLE STAPHYLOCOCCUS AUREUS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; REACTION TIME; STRUCTURE ACTIVITY RELATION; THERAPY EFFECT; VANCOMYCIN RESISTANT ENTEROCOCCUS;

ANTI-BACTERIAL AGENTS; DEPSIPEPTIDES; DRUG DESIGN; LYSOBACTER; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; MICROBIAL SENSITIVITY TESTS; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84897148889     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2013.128     Document Type: Article

References (14)

1. Rice, L. B. The clinical consequences of antimicrobial resistance. Curr. Opin. Microbiol. 12, 476-481 (2009
2. Cai, J. C. et al. Linezolid-resistant clinical isolates of meticillin-resistant coagulasenegative staphylococci and Enterococcus faecium from China. J. Med. Microbiol. 61, 1568-1573 (2012
3. Sawa, R. et al. Amycolamicin: A novel broad-spectrum antibiotic inhibiting bacterial topoisomerase. Chem. Eur. J. 18, 15772-15781 (2012
4. Hashizume, H.et al. Tripropeptins, novel antimicrobial agents produced by Lysobacter sp. I. Taxonomy, isolation and biological activities. J. Antibiot. 54, 1054-1059 (2001
5. Hashizume, H.et al. Tripropeptins, novel antimicrobial agents produced by Lysobacter sp. II. Structure elucidation. J. Antibiot. 57, 52-58 (2004
6. 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
7. 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
8. Shoji, J.et al. Isolation and characterization of new peptide antibiotics, plusbacins A1- A4 and B1-B4. J. Antibiot. 45, 817-823 (1992
9. Shoji, J. et al. Structure of new peptide antibiotics, plusbacins A1-A4 and B1-B4. J. Antibiot. 45, 824-831 (1992
10. Konishi, M. et al. Empedopeptin (BMY-28117), a new depsipeptide antibiotic. I. Production, isolation and properties. J. Antibiot. 37, 949-957 (1984
11. Sugawara, K., Numata, K., Konishi, M. & Kawaguchi, H. Empedopeptin (BMY-28117), a new depsipeptide antibiotic. II. Structure determination. J. Antibiot. 37, 958-964 (1984
12. 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
13. 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
14. 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)