NMR-based assignment of isoleucine vs. allo-isoleucine stereochemistry. Issue 44 (1st November 2017)

• Record Type: Journal Article
• Authors: Anderson, Zoe J.; Hobson, Christian; Needley, Rebecca; Song, Lijiang; Perryman, Michael S.; Kerby, Paul; Fox, David J.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 44(2017)
• Page Start: 9372
• Page End: 9378
• Publication Date: 2017-11-01
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob01995e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A simple 1 H and 13 C 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. Abstract : A simple 1 H and 13 C 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.