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

Angewandte Chemie
Kiri A ThornalleyDavid K Smith

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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Citations

Feb 28, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Domenico MarsonSabrina Pricl
Oct 24, 2018·Proceedings of the National Academy of Sciences of the United States of America·Philippe GarrigueLing Peng
Feb 11, 2021·Chemical Communications : Chem Comm·Diksha GambhirRik Rani Koner
Nov 5, 2019·ACS Chemical Biology·Benjamin Ourri, Laurent Vial
Sep 8, 2020·Journal of the American Chemical Society·Fang WangHuibin Qiu

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