P Le Roux, D Blanot, D Mengin-Lecreulx, J Van Heijenoort
{"title":"Peptides containing 2-aminopimelic acid. Synthesis and study of in vitro effects on bacterial cells.","authors":"P Le Roux, D Blanot, D Mengin-Lecreulx, J Van Heijenoort","doi":"","DOIUrl":null,"url":null,"abstract":"<p><p>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(Cl)-ambo-Apm and ambo-Apm-L-Ala(Cl). In the two latter cases, Apm was associated with antibacterial amino acid beta-chloro-L-alanine [L-Ala(Cl)], an inhibitor of alanine racemase and transaminase B. The peptides displayed weak or no antibacterial activities; nevertheless, those containing L-Ala(Cl) 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(Cl)-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.</p>","PeriodicalId":14204,"journal":{"name":"International journal of peptide and protein research","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"1991-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"International journal of peptide and protein research","FirstCategoryId":"1085","ListUrlMain":"","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
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(Cl)-ambo-Apm and ambo-Apm-L-Ala(Cl). In the two latter cases, Apm was associated with antibacterial amino acid beta-chloro-L-alanine [L-Ala(Cl)], an inhibitor of alanine racemase and transaminase B. The peptides displayed weak or no antibacterial activities; nevertheless, those containing L-Ala(Cl) 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(Cl)-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.
利用肽转运策略,我们设计并合成了几种新的含有2-氨基苯基酸(Apm)的肽:L-Lys-ambo-Apm、ambo-Apm-L-Lys、L-Lys-L-Ala-ambo-Apm、L-Ala(Cl)-ambo-Apm和ambo-Apm-L-Ala(Cl)。在后两种情况下,Apm与抗菌氨基酸β -氯- l -丙氨酸[L-Ala(Cl)]相关,该氨基酸是丙氨酸消旋酶和转氨酶b的抑制剂。然而,那些含有L-Ala(Cl)的氨基酸在恢复蛋白质合成的氨基酸存在下具有较低的MIC值。在最小培养基中培养的指数期大肠杆菌细胞上进行实验时,这些肽没有作用或抑菌作用,但当生长培养基中添加特定氨基酸时,可以观察到重要的抑菌作用,特别是含有L-Ala(Cl)的肽。结果表明,含l -赖氨酸肽的弱效应或零效应是由于摄取不良。