NMR-based assignment of isoleucine vs. allo-isoleucine stereochemistry

Organic & Biomolecular Chemistry
Zoe J AndersonDavid J Fox

Abstract

A simple 1H and 13C NMR spectrometric analysis is demonstrated that permits differentiation of isoleucine and allo-isoleucine residues by inspection of the chemical shift and coupling constants of the signals associated with the proton and carbon at the α-stereocentre. This is applied to the estimation of epimerisation during metal-free N-arylation and peptide coupling reactions.

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