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NMR-based assignment of isoleucine vs allo-isoleucine stereochemistry
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Anderson, Zoe J., Hobson, Christian, Needley, Rebecca, Song, Lijiang, Perryman, Michael S., Kerby, Paul D. and Fox, David J. (2017) NMR-based assignment of isoleucine vs allo-isoleucine stereochemistry. Organic & Biomolecular Chemistry, 15 (44). 9372-9378 . doi:10.1039/C7OB01995E ISSN 1477-0520.
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Official URL: http://doi.org/10.1039/C7OB01995E
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.
| Item Type: | Journal Article | |||||||||
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| Subjects: | Q Science > QD Chemistry | |||||||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||
| Library of Congress Subject Headings (LCSH): | Stereochemistry, Nuclear magnetic resonance spectroscopy, Peptides, Amino acids | |||||||||
| Journal or Publication Title: | Organic & Biomolecular Chemistry | |||||||||
| Publisher: | Royal Society of Chemistry | |||||||||
| ISSN: | 1477-0520 | |||||||||
| Official Date: | 1 November 2017 | |||||||||
| Dates: |
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| Volume: | 15 | |||||||||
| Number: | 44 | |||||||||
| Page Range: | 9372-9378 | |||||||||
| DOI: | 10.1039/C7OB01995E | |||||||||
| Status: | Peer Reviewed | |||||||||
| Publication Status: | Published | |||||||||
| Access rights to Published version: | Open Access (Creative Commons) | |||||||||
| Date of first compliant deposit: | 25 September 2017 | |||||||||
| Date of first compliant Open Access: | 28 March 2018 | |||||||||
| RIOXX Funder/Project Grant: |
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