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Issue 44, 2017
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NMR-based assignment of isoleucine vs. allo-isoleucine stereochemistry

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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.

Graphical abstract: NMR-based assignment of isoleucine vs. allo-isoleucine stereochemistry

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Article information


Submitted
10 Aug 2017
Accepted
19 Sep 2017
First published
01 Nov 2017

This article is Open Access

Org. Biomol. Chem., 2017,15, 9372-9378
Article type
Paper

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

Z. J. Anderson, C. Hobson, R. Needley, L. Song, M. S. Perryman, P. Kerby and D. J. Fox, Org. Biomol. Chem., 2017, 15, 9372
DOI: 10.1039/C7OB01995E

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