Total synthesis and membrane modifying properties of the lipopeptaibol trikoningin KB II and its analogues with acyl chains of different length at the N- and C-termini.
Trikoningin KB II, a ten-amino acid residue lipopeptaibol blocked at the N-terminus by the n-octanoyl group and at the C-terminus by the 1,2-amino alcohol L-leucinol, and extracted from the fungus Trichoderma koningii, exhibits membrane-modifying properties. We have synthesized by solution-phase methods trikoningin KB II and several analogues with acyl chains of different length at the N- and C-termini. Permeability measurements showed that an appropriate length of the linear acyl chain is a more important characteristic for the onset of significant membrane-modifying activity than its position in the peptide chain.
Piazza
C
C
Department of Organic Chemistry, Biopolymer Research Centre, C.N.R., University of Padova, Italy.
Formaggio
F
F
Crisma
M
M
Toniolo
C
C
Kamphuis
J
J
Kaptein
B
B
Broxterman
Q B
QB
D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002463:Cell Membrane Permeability / Q000187:drug effects*; D006020:Glycopeptides; D055666:Lipopeptides; D008081:Liposomes / Q000187:drug effects; D054848:Peptaibols; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D006020:Glycopeptides; D055666:Lipopeptides; D008081:Liposomes; D054848:Peptaibols; D010455:Peptides; C116419:trichogin GA IV; C119177:trikoningin KB II