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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

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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.

Item Type: Journal Article
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:
DateEvent
1 November 2017Available
19 September 2017Accepted
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:
Project/Grant IDRIOXX Funder NameFunder ID
UNSPECIFIED[EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
UNSPECIFIEDUniversity of Warwickhttp://dx.doi.org/10.13039/501100000741
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