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Application of the TORO technique of 1H NMR to the structural analysis of cyclic peptide isomers having a slightly distorted symmetry from C2

✍ Scribed by Eiji Watanabe; Makoto Tamaki; Fumiyuki Yamakura; Minoru Akiyama

Publisher: John Wiley and Sons
Year: 2003
Tongue: English
Weight: 177 KB
Volume: 42
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1310

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✦ Synopsis

Abstract

The extended TORO technique was applied to the structural analysis of endo‐D‐Tyr‐gramicidin S, cyclo(‐Val‐Orn‐Leu‐D‐Phe‐D‐Tyr‐Pro‐Val‐Orn‐Leu‐D‐Phe‐Pro‐), which has a slightly distorted symmetry from C~2~, by the insertion of D‐Tyr and equivalent α‐proton chemical shifts in the ^1^H NMR spectrum. All NMR signals of the two dominant isomers of this antibiotic with trans–trans prolines were determined by using the extended TORO technique with TOCSY and ROESY spectra. This technique is generally applicable for distinguishing overlapped signals of α‐ and amide protons from the main chains of peptides. Copyright © 2003 John Wiley & Sons, Ltd.

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