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Enantiomeric and Diastereomeric Self‐Assembled Multivalent Nanostructures: Understanding the Effects of Chirality on Binding to Polyanionic Heparin and DNA
Author(s) -
Thornalley Kiri A.,
Laurini Erik,
Pricl Sabrina,
Smith David K.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201803298
Subject(s) - diastereomer , chemistry , enantiomer , cationic polymerization , chirality (physics) , stereochemistry , self assembly , enantioselective synthesis , dna , lysine , supramolecular chemistry , combinatorial chemistry , amino acid , organic chemistry , biochemistry , molecule , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
A family of four self‐assembling lipopeptides containing Ala‐Lys peptides attached to a C 16 aliphatic chain were synthesised. These compounds form two enantiomeric pairs that bear a diastereomeric relationship to one another (C 16 ‐ l ‐Ala‐ l ‐Lys/C 16 ‐ d ‐Ala‐ d ‐Lys) and (C 16 ‐ d ‐Ala‐ l ‐Lys/C 16 ‐ 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.