Trichogin: a paradigm for lipopeptaibols.
Lipopeptaibols are members of a novel family of naturally occurring, short peptides with antimicrobial activity, characterized by a lipophilic acyl chain at the N-terminus, a high content of turn/helix inducing alpha-aminoisobutyric acid and a 1,2-amino alcohol at the C-terminus. Using solution methods, the prototypical lipopeptaibol trichogin GA IV and a large series of appropriately designed analogues were synthesized, which allow: (i) determination of the minimal lipid chain and peptide main-chain lengths for the onset of membrane activity, and (ii) exploitation of a number of physico-chemical techniques aimed at assessing the trichogin preferred conformation under a variety of conditions and at investigating its mechanism of interaction with the phospholipid membranes.
Peggion
Cristina
C
Institute of Biomolecular Chemistry, CNR, Department of Organic Chemistry, University of Padova, 35131 Padova, Italy.
Formaggio
Fernando
F
Crisma
Marco
M
Epand
Raquel F
RF
Epand
Richard M
RM
Toniolo
Claudio
C
D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D005656:Fungal Proteins / Q000737:chemistry*; D006020:Glycopeptides; D057927:Hydrophobic and Hydrophilic Interactions; D055666:Lipopeptides; D008074:Lipoproteins / Q000138:chemical synthesis; D008081:Liposomes / Q000378:metabolism; D010455:Peptides; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D005656:Fungal Proteins; D006020:Glycopeptides; D055666:Lipopeptides; D008074:Lipoproteins; D008081:Liposomes; D010455:Peptides; C116419:trichogin GA IV