Trifluoroacetylation and Sulfur Oxidation States Modulate Cis-Trans Isomerization and Atropisomerism in N-Aryl Peptoids.

Authors

Nithin Kumara Mothahalli Raju, Bishwajit Paul, Jayprakash Prajapati, Sourav Chatterjee, Epari Sai Santosh Kumar, Kshatresh Dutta Dubey

Published in

Chirality. Volume 38. Issue 9. Pages e70147.

Abstract

Trifluoroacetylation and varying sulfur oxidation states can modulate the stereodynamic features in N-aryl peptoids. This study elucidates the restricted rotation about both the chiral C_aryl-N axis and the N-C(O) amide bond, highlighting the inherently flexible nature of tertiary amide scaffolds. Tertiary amide bond isomerization, axial chirality, and multiple stereochemical forms were investigated utilizing ¹⁹F NMR, dynamic HPLC, crystallographic studies, and computational analysis. Notably, the introduction of a sulfoxide moiety as an auxiliary stereogenic element facilitates the formation of multiple and distinct stereochemical forms, as evident from ¹⁹F NMR studies and computational modeling. These structural modifications can provide a robust platform to understand stereodynamic features in N-aryl peptoids.

PMID:
42683941
Bibliographic data and abstract were imported from PubMed on 02 Sep 2026.

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