A family of four self-assembling lipopeptides containing Ala-Lys peptides attached to a C aliphatic chain were synthesised. These compounds form two enantiomeric pairs that bear a diastereomeric relationship to one another (C -l-Ala-l-Lys/C -d-Ala-d-Lys) and (C -d-Ala-l-Lys/C -l-Ala-d-Lys). These diastereomeric pairs have very different critical micelle concentrations (CMCs). The self-assembled multivalent (SAMul) systems bind biological polyanions as a result of the cationic lysine groups on their surfaces. For heparin binding, there was no significant enantioselectivity, but there was a binding preference for the diastereomeric assemblies with lower CMCs. Conversely, for DNA binding, there was significant enantioselectivity for systems displaying d-lysine ligands, with a further slight preference for attachment to l-alanine, with the CMC being irrelevant.
Af amily of four self-assembling lipopeptides containing Ala-Lys peptides attached to aC 16 aliphatic chain were synthesised. These compounds form two enantiomeric pairs that bear ad iastereomeric relationship to one another (C 16 -l-Ala-l-Lys/C 16 -d-Ala-d-Lys) and (C 16 -d-Ala-l-Lys/C 16l-Ala-d-Lys). These diastereomeric pairs have very different critical micelle concentrations (CMCs). The self-assembled multivalent (SAMul) systems bind biological polyanions as ar esult of the cationic lysine groups on their surfaces.F or heparin binding,there was no significant enantioselectivity,but there was ab inding preference for the diastereomeric assemblies with lower CMCs.C onversely,f or DNAb inding,t here was significant enantioselectivity for systems displaying d-lysine ligands,with afurther slight preference for attachment to l-alanine,with the CMC being irrelevant.
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