Cyclic arylopeptoid oligomers: synthesis and conformational propensities of peptide-mimetic aromatic macrocycles

Organic & Biomolecular Chemistry
Masahide HayakawaMasato Ikeda

Abstract

Macrocyclic peptide-mimetic molecules are attracting renewed attention and have found widespread application in research fields ranging from biochemical science to materials science. Herein, we describe the synthesis and structural elucidation of cyclo[n]-p-arylopeptoids (classified into cyclic aromatic ε-amino acids) bearing various side chains, namely, C[n]pAP(Rn) (where n inside brackets denotes the number of main chain units and R inside parentheses represents side chains). We investigate the influence of n and R on the macrocyclization efficiency of linear p-arylopeptoid oligomers (n = 3, 4, 5) under high-dilution conditions with or without slow addition. The structures of the cyclo[4]-p-arylopeptoids (C[4]pAP(Rn)) and their conformational dynamics are disclosed on the basis of single-crystal X-ray analyses, viable-temperature (VT) 1H NMR studies, and density functional theory (DFT) calculations. We found two representative conformations (open and closed) of cyclo[4]-p-arylopeptoids (C[4]pAP(Rn)) in the solid state and whose preference in the solution state was most likely dependent on solvent polarity. We believe that this simple but dynamic macrocyclic peptide-mimetic molecular scaffold would be attractive for developing...Continue Reading

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Citations

May 10, 2019·Biopolymers·Adrian S Culf
Oct 3, 2020·International Journal of Molecular Sciences·Anastasia NazarovaIvan Stoikov
Sep 20, 2019·Organic Letters·Joseph W MeiselAndrew D Hamilton

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Methods Mentioned

BETA
X-ray
NMR
size exclusion column chromatography
size exclusion chromatography

Software Mentioned

HyperChem

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