Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
Simulation Engineering (MOSE) Laboratory, Department of Engineering and Architectures (DEA), University of Trieste, 34127, Trieste, Italy.
Angew Chem Int Ed Engl. 2018 Jul 9;57(28):8530-8534. doi: 10.1002/anie.201803298. Epub 2018 Jun 12.
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.
合成了含有连接到 C 脂族链的 Ala-Lys 肽的四种四元自组装脂肽。这些化合物形成了两对对映异构体，彼此具有非对映关系（C-l-Ala-l-Lys/C-d-Ala-d-Lys）和（C-d-Ala-l-Lys/C-l-Ala-d-Lys）。这些非对映异构体对具有非常不同的临界胶束浓度（CMC）。自组装多价（SAMul）系统由于表面上的阳离子赖氨酸基团而结合生物多阴离子。对于肝素结合，没有明显的对映选择性，但对于 CMC 较低的非对映异构体组装体具有结合偏好。相反，对于 DNA 结合，对于显示 d-赖氨酸配体的系统具有显著的对映选择性，对于与 l-丙氨酸结合的系统略有偏好，CMC 无关紧要。
