Helical peptaibol mimics are better ionophores when racemic than when enantiopure.
Helical peptide foldamers rich in α-aminoisobutyric acid (Aib) act as peptaibol-mimicking ionophores in the phospholipid bilayers of artificial vesicles. Racemic samples of these foldamers are more active than their enantiopure counterparts, which was attributed to differing propensities to form aggregates with crystal-like features in the bilayer.
School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK. j.clayden@bristol.ac.uk.
Sarah J
SJ
Pike
Jennifer E
JE
Jones
James
J
Raftery
Jonathan
J
Clayden
Simon J
SJ
Webb
D000613:Aminobutyrates / Q000737:chemistry; D007476:Ionophores / Q000737:chemistry* / Q000494:pharmacology*; D008051:Lipid Bilayers / Q000737:chemistry / Q000378:metabolism; D008958:Models, Molecular; D008968:Molecular Conformation; D054848:Peptaibols / Q000737:chemistry*; D057786:Peptidomimetics / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000613:Aminobutyrates; D007476:Ionophores; D008051:Lipid Bilayers; D054848:Peptaibols; D057786:Peptidomimetics; C012223:alpha-aminobutyric acid