Self-Assembly of Amphiphilic Dipeptide with Homo- and Heterochiral Centers and Their Application in Asymmetric Aldol Reaction.

ABSTRACT: Chiral self-assembly has drawn increasing interest in supramolecular chemistry. Here, we have designed amphiphilic l-Pro-l-Glu and l-Pro-d-Glu dipeptides and investigated their chiral self-assembly as well as asymmetric catalytic performance to disclose the synergistic effect of two stereogenic centers in the self-assembly and catalysis. It was found that both of the diastereomeric dipeptides can easily self-assemble into organogels with nanofibers. When these nanofibers were used as a catalyst for the asymmetric aldol reactions, enhanced enantioselectivity was obtained compared with their molecular state. Moreover, the L-L isomer assemblies showed higher enantioselectivity than the L-D isomer. It was revealed that both the supramolecular chirality of the nanofiber and the chiral catalytic

SUBMITTER: Bhowmick S 

PROVIDER: S-EPMC6644911 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature