The invention relates to peptides having a highly effective antimicrobial activity, processes for the preparation thereof, and the use thereof.
It is known that naturally occurring peptides may be antibiotically effective. Thus, WO 97/35877 describes the occurrence and purification of antibiotic peptides from cow\'s milk, and PCT/EP 01/06518 describes the recovery of antimicrobial peptides from human placenta extract and from bovine thymus extract, and their application.
One of the peptides purified from bovine thymus extract is bolisin (PCT/EP 01/06518, SEQ ID No. 5). Bolisin is a fragment of the bovine mitochondrial proteolipid comprising 17 amino acids, and it inhibits the growth of pathogenic microorganisms in low-salt nutrient media.
It is an object of the invention to provide bolisin-based peptides which have a particularly high specific activity under different conditions. It is also an object of the invention to provide peptides which inhibit the growth of microorganisms in environments with physiological salt concentrations and at the same time have as low as possible a hemolytic activity.
Surprisingly, this object is achieved by providing peptides of the sequence
R1-ZX3X3X1BX3RX2X3X4BRX2BX3X3B—R2,
wherein
R1 represents an amino group (NH2), an amino acid or a peptide having up to 10 amino acids, and R2 represents COOH, CONH2, an amino acid or a peptide having up to 10 amino acids;
Z represents an aromatic amino acid (W, Y, F), preferably tyrosine (Y) or an amino acid mono- or polyhalogenated at the aromatic moiety, preferably tyrosine (Y);
X1 represents arginine (R) or an aromatic amino acid (W, Y, F), preferably tryptophan (W) or an amino acid mono- or polyhalogenated at the aromatic moiety, preferably tryptophan;
X2 represents serine (S), a basic amino acid (R, K), preferably arginine (R), or an aromatic amino acid (W, Y, F), preferably tryptophan (W) or an amino acid mono- or polyhalogenated at the aromatic moiety, preferably tryptophan;
X3 represents threonine (T), a hydrophobic amino acid (I, V, A, L) or arginine (R);
X4 represents aspartic acid (D), proline (P), a basic amino acid (K, R), preferably arginine (R), or an aromatic amino acid (W, Y, F), preferably tryptophan (W) or an amino acid mono- or polyhalogenated at the aromatic moiety, preferably tryptophan; and
B represents a basic amino acid (K, R).
The invention also relates to derivatives and/or fragments of the peptides according to the invention having antimicrobial activity, especially the derivatives and/or fragments which are amidated, acylated, acetylated, alkylated, sulfated, phosphorylated, halogenated, especially halogenated at aromatic amino acid side chains, glycosylated, oxidized, modified by esterification or lactone formation, and/or cyclized. Halogenated peptides are preferably halogenated at aromatic residues of amino acid side chains. The amino acids are designated with the one-letter code.
Preferably, the peptides according to the invention have the following sequences:
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