Unique β-Turn Peptoid Structures and their Application as Asymmetric Catalysts.

Unique β-Turn Peptoid Structures and their Application as Asymmetric Catalysts.
Chemistry. 2020 Mar 26;:
Authors: Drapaneni C, Ghosh P, Ghosh T, Maayan G
Abstract
Peptoids - N-substituted glycine oligomers - represent an important class of peptidomimetics that can fold into three-dimensional structures in solution. Most of the folded peptoid structures, however, resemble helices, and this can limit their applications, specifically in asymmetric catalysis. Herein we describe, for the first time, unique examples of pyrrolidine-based β-turn-like peptoids and characterize them both in the solid state by single crystal X-ray analysis and in solution by circular dichroism spectroscopy. Furthermore, we demonstrate their highly efficient and enantioselective catalytic activity for the production of γ-nitro aldehydes via asymmetric Michael reaction in water. The structural properties and DFT-D3 calculations of the new β-turn-like peptoids, as well as catalytic and spectroscopic studies on designed pyrrolidine-based helical peptoids, suggest that the β-turn structure plays a key role in the stereoselectivity of the catalytic reaction.
PMID: 32216133 [PubMed - as supplied by publisher]

Source: Chemistry - March 25, 2020 Category: Chemistry Authors: Drapaneni C, Ghosh P, Ghosh T, Maayan G Tags: Chemistry Source Type: research