Synthesis of a chiral amino acid with bicyclo[1.1.1]pentane moiety and its incorporation into linear and cyclic antimicrobial peptides.
The synthesis of the lipophilic chiral amino acid 1 bearing the bicyclo[1.1.1]pentane moiety is described. Linear and cyclic hexapeptides of the type Arg-Arg-Xaa-Yaa-Arg-Phe containing 1 instead of one or two tryptophan residues are prepared by solid phase peptide synthesis and the antimicrobial and hemolytic activity of the peptides obtained are discussed.
Pritz
Stephan
S
Leibniz-Institute of Molecular Pharmacology, Robert-Rössle-Strasse 10, 13125, Berlin, Germany. pritz@fmp-berlin.de
Pätzel
Michael
M
Szeimies
Günter
G
Dathe
Margitta
M
Bienert
Michael
M
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D023181:Antimicrobial Cationic Peptides / Q000737:chemistry* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D010420:Pentanes / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000737:chemistry*; D013997:Time Factors
D000596:Amino Acids; D023181:Antimicrobial Cationic Peptides; D010420:Pentanes; D010456:Peptides, Cyclic; C033353:pentane