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Fettsäurehaltige basische Peptide mit antibakterieller Wirkung
Author(s) -
Vogler K.,
Lanz P.,
Quitt P.,
Studer R. O.,
Lergier W.,
Böhni E.,
Fust B.
Publication year - 1964
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19640470220
Subject(s) - chemistry , residue (chemistry) , lysine , peptide , amino acid , amide , stereochemistry , palmitic acid , peptide synthesis , organic chemistry , fatty acid , biochemistry
The synthesis of a new class of surface active agents consisting of basic peptides containing on one amino group a large aliphatic acyl residue is outlined. There are some definite relations between constitution and antibacterial properties. The structural conditions for maximum activity are: 1 The peptide has to consist of strongly basic amino‐acids. Lysine as an inexpensive constituent seems to be the material of choice. 2 Lengthening of the peptide chain in the oligo series is associated with increasing activity, but lysine dipeptides show optimal properties. 3 The aliphatic fatty acid residue has to contain preferably 14‐18 carbon atoms, palmitic acid representing the optimum. I t should be attached to the Na‐amino group. 4 The carboxyl end has to be protected, e. g. by an ester or amide function, in order to avoid a decrease in basicity. 5 Lower units such as acylated basic amino‐acids exhibit lower activity, especially against G RAM ‐negative pathogens.