NMR-based assignment of isoleucine vs. allo-isoleucine stereochemistry,Organic & Biomolecular Chemistry

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NMR-based assignment of isoleucine vs. allo-isoleucine stereochemistry
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2017-11-01 00:00:00 , DOI: 10.1039/c7ob01995e
Zoe J. Anderson _{1,

2,

3,

4} , Christian Hobson _{1,

2,

3,

4} , Rebecca Needley _{1,

2,

3,

4} , Lijiang Song _{1,

2,

3,

4} , Michael S. Perryman _{1,

2,

3,

4} , Paul Kerby _{1,

2,

3,

4} , David J. Fox _{1,

2,

3,

4}

Affiliation

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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