Part of this work has been presented at the 20th European Peptide Symposium (Tübingen, FRG, September 1988) (1). Abbreviations for amino acids, peptides, and their derivatives are those recommended by the IUPAC-IUB (European J. Biochem. 1984, 138, 9–37). In particular, the prefix ambo is used instead of the symbol DL in diastereoisomeric peptides whose ratio may not be unity.
Peptides containing 2-aminopimelic acid
Synthesis and study of in vitro effects on bacterial cells*
Article first published online: 12 JAN 2009
International Journal of Peptide and Protein Research
Volume 37, Issue 2, pages 103–111, February 1991
How to Cite
LE ROUX, P., BLANOT, D., MENGIN-LECREULX, D. and VAN HEIJENOORT, J. (1991), Peptides containing 2-aminopimelic acid. International Journal of Peptide and Protein Research, 37: 103–111. doi: 10.1111/j.1399-3011.1991.tb00089.x
- Issue published online: 12 JAN 2009
- Article first published online: 12 JAN 2009
- Received 5 March, accepted for publication 8 August 1990
- l-2-aminopimelic acid;
- antibacterial peptides;
- diaminopimelate pathway
Taking advantage of the peptide transport strategy, we have designed and synthesized several new peptides containing 2-aminopimelic acid (Apm), an inhibitor of the diaminopimelate pathway in bacteria: L-LYS-ambo-Apm, ambo-Apm-L-Lys, L-Lys-L-Ala-ambo-Apm, ambo-Apm-L-Ala-L-Lys, L-Ala(CI)-ambo-Apm and ambo-Apm-L-Ala(CI). In the two latter cases, Apm was associated with antibacterial amino acid β-chloro-L-alanine [L-Ala(CI)], an inhibitor of alanine racemase and transaminase B. The peptides displayed weak or no antibacterial activities; nevertheless, those containing L-Ala(CI) had low MIC values in the presence of amino acids restoring protein synthesis. When tested on exponential phase Escherichia coli cells grown in minimal medium, the peptides were without effect or bacteriostatic, but important bacteriolytic effects could be observed, especially for the L-Ala(CI)-containing peptides, when the growth medium was supplemented with specific amino acids. It was demonstrated that the weak or nil effect of the L-lysine-containing peptides was due to a poor uptake.