Issue 28, 2021

Effect of C12H25O– substituent position on the self-assembly behaviour of C6H5COO–Ala–Ala dipeptide

Abstract

Three dipeptides based on the Ala–Ala building block with different substituent positions of the dodecyloxy group on the benzoyl residue at the N terminus were designed and synthesized (ortho-, meta- and para-16). All of them were able to spontaneously self-assemble in the mixed solvent of methanol and water (6/4, v/v). However, three dipeptides underwent a distinct kinetically controlled self-assembling process. The spectroscopic study also revealed that, for ortho-16, the phenylene groups and the peptide sequence loosely packed, while meta- and para-16 stacked into well-ordered structures with the formation of parallel β-sheets through supramolecular self-assembly. Intramolecular hydrogen bonding and steric hindrance of the dodecyloxy side chain were proposed to lead to the different self-assembling behaviour of the three isomers.

Graphical abstract: Effect of C12H25O– substituent position on the self-assembly behaviour of C6H5COO–Ala–Ala dipeptide

Supplementary files

Article information

Article type
Paper
Submitted
09 Mar 2021
Accepted
09 Jun 2021
First published
10 Jun 2021

New J. Chem., 2021,45, 12585-12592

Effect of C12H25O– substituent position on the self-assembly behaviour of C6H5COO–Ala–Ala dipeptide

S. Lin, Q. Tong, P. Jiang, B. Li, Y. Li and Y. Yang, New J. Chem., 2021, 45, 12585 DOI: 10.1039/D1NJ01148K

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