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Enantiomeric and Diastereomeric Self-Assembled Multivalent Nanostructures: Understanding the Effects of Chirality on Binding to Polyanionic Heparin and DNA

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JournalAngewandte Chemie International Edition
DateAccepted/In press - 15 May 2018
DateE-pub ahead of print - 12 Jun 2018
DatePublished (current) - 9 Jul 2018
Issue number28
Volume57
Number of pages5
Pages (from-to)8530-8534
Early online date12/06/18
Original languageEnglish

Abstract

A family of four self-assembling lipopeptides containing Ala-Lys peptides attached to a C16 aliphatic chain were synthesised. These compounds form two enantiomeric pairs that bear a diastereomeric relationship to one another (C16-l-Ala-l-Lys/C16-d-Ala-d-Lys) and (C16-d-Ala-l-Lys/C16-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.

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© 2018 Wiley‐VCH Verlag. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

    Research areas

  • DNA, heparin, multivalency, self-assembly, supramolecular chemistry

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