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The synthesis and biological activity of some diamino acid analogs

1958; Elsevier BV; Volume: 76; Issue: 1 Linguagem: Inglês

10.1016/0003-9861(58)90128-0

1096-0384

Alvie L. Davis, Joanne M. Ravel, Charles G. Skinner, William Shive,

Antimicrobial Peptides and Activities

Abstract 3- and 4-Aminocyclohexanealanine, 4-aminocyclohexaneglycine, and the corresponding phenyl analogs have been prepared and studied as amino acid antagonists for Escherichia coli, Leuconostoc dextranicum, Lactobacillus casei, and Lactobacillus arabinosus. The compounds which were most effective include 3-aminocyclohexanealanine, m-aminophenylalanine, and p-aminophenylalanine. Growth inhibition effected by 3-aminocyclohexanealanine was reversed competitively over a range of inhibitor concentrations by increasing concentrations of lysine but not by phenylalanine, while the toxicity of the phenyl analogs was reversed over a broad range of inhibitor concentrations by phenylalanine but not by lysine. The inactivity of 4-aminocyclohexaneglycine suggests that either branching of the carbons at the β- rather than the γ-carbon sterically hinders its enzymic combination, or that the conformation of lysine on the inhibited enzyme exists in a manner such that the γ- and ϵ-carbons must be in a trans-like relationship, which is possible for the 3-aminocyclohexanealanine but not for the 4-aminocyclohexaneglycine.