Lipopeptaibols, a novel family of membrane active, antimicrobial peptides.
Lipopeptaibols are members of a novel group of naturally occurring, short peptides with antimicrobial activity, characterized by a lipophilic acyl chain at the N-terminus, a high content of the turn/helix forming alpha-aminoisobutyric acid and a 1,2-amino alcohol at the C-terminus. The amino acid sequences range from 6 to 10 residues and the fatty acyl moieties from 8 to 15 carbon atoms. The peptide portion of lipopeptaibols can be shorter than those of the nonlipidated peptaibols that range from 10 to 19 amino acid residues. The longest peptides fold into a mixed 3(10)/alpha helix, whereas the shortest peptides tend to adopt a beta-turn/sheet structure. Using solution methodologies, a series of analogues of trichogin GA IV was synthesized which allowed determination of the minimal lipid chain and peptide main-chain lengths for the onset of membrane activity and exploitation of a number of spectroscopic techniques aimed at determining its preferred conformation under a variety of conditions and investigating in detail its mode of interaction with, and its effect on, the phospholipid membranes.
Toniolo
C
C
Biopolymer Research Center, CNR, Department of Organic Chemistry, University of Padova, Italy. biop02@chor.unipd.it
Crisma
M
M
Formaggio
F
F
Peggion
C
C
Epand
R F
RF
Epand
R M
RM
D000595:Amino Acid Sequence; D000621:Aminoisobutyric Acids / Q000032:analysis; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D023181:Antimicrobial Cationic Peptides; D002462:Cell Membrane / Q000648:ultrastructure; D005231:Fatty Acids, Unsaturated / Q000737:chemistry; D006020:Glycopeptides; D019077:Helix-Turn-Helix Motifs; D055666:Lipopeptides; D008958:Models, Molecular; D009842:Oligopeptides / Q000737:chemistry; D054848:Peptaibols; D010455:Peptides; D011487:Protein Conformation; D016415:Sequence Alignment; D017386:Sequence Homology, Amino Acid
D000621:Aminoisobutyric Acids; D000900:Anti-Bacterial Agents; D023181:Antimicrobial Cationic Peptides; D005231:Fatty Acids, Unsaturated; D006020:Glycopeptides; D055666:Lipopeptides; D009842:Oligopeptides; D054848:Peptaibols; D010455:Peptides; C116419:trichogin GA IV; C119177:trikoningin KB II; C087389:trichodecenin II; C087388:trichodecenin I; C100049:2-aminoisobutyric acid; C016160:trichopolyn