Peptides having antimicrobial activity and new enzyme capable of converting L-configured residue in D-configured amino acid in a peptide
The present invention relates to a new class of peptides having antibacterial activity and presenting D-amino acids and their uses. It also relates to a new enzyme presenting a peptide epimerase activity in vitro and in vivo, thereby being useful for modifying peptides in order to change the amino acid configuration from L to D.
1. A peptide 17 to 25 amino acids in length and in which the amino acids [V/I/A] in position 4 and 12 of the sequence as set forth in the following SEQ ID NOs have a D-configuration, wherein:
a) the peptide contains SEQ ID NO: 66, 67, or 68;
b) the peptide contains SEQ ID NO: 77;
c) the peptide contains SEQ ID NO: 78;
d) the peptide contains SEQ ID NO: 79; or
e) the peptide contains SEQ ID NO: 73 and the peptide has at least one modification selected from the group consisting of N-acetylation, acylation, C-amidation, a (CH 2 NH) reduced bond, a (NHCO) retro-inverso bond, a (CH 2 -O) methylene-oxy bond, a (CH 2 -S) thiomethylene bond, a (CH 2 CH 2 ) carba bond, a (CO—CH 2 ) cetomethylene bond, a (CHOH—CH 2 ) hydroxyethylene bond, a (N—N) bound, a E-alcene bond and a —CH═CH-bond.
2. The peptide according to claim 1 , wherein the peptide contains SEQ ID NO: 66.
3. The peptide according to claim 1 , wherein the peptide contains SEQ ID NO: 67.
4. The peptide according to claim 1 , wherein the peptide contains SEQ ID NO: 68.
5. The peptide according to claim 1 , wherein the peptide contains SEQ ID NO: 77.
6. The peptide according to claim 1 , wherein the peptide contains SEQ ID NO: 78.
7. The peptide according to claim 1 , wherein the peptide contains SEQ ID NO: 79.
8. The peptide of claim 1 , wherein the peptide is between 17 to 25 amino acids in length, has at least two D-configured amino acids and contains SEQ ID NO: 73, wherein the amino acids [V/I/A] in position 4 and 12 have a D-configuration and the peptide has at least one modification selected from the group consisting of N-acetylation, acylation, C-amidation, a (CH 2 NH) reduced bond, a (NHCO) retro-inverso bond, a (CH 2 -O) methylene-oxy bond, a (CH 2 -S) thiomethylene bond, a (CH 2 CH 2 ) carba bond, a (CO—CH 2 ) cetomethylene bond, a (CHOH—CH 2 ) hydroxyethylene bond, a (N—N) bound, a E-alcene bond and a —C═CH-bond.
9. A pharmaceutical or veterinary composition comprising the peptide according to claim 1 .
10. A medical device or implant comprising a body having at least one surface coated with or including the peptide of claim 1 .
11. A disinfectant or preservative composition comprising the peptide of claim 1 .