Issue 95, 2017

Synthesis and shift-reagent-assisted full NMR assignment of bacterial (Z8,E2,ω)-undecaprenol

Abstract

The repeating isoprene unit is a fundamental biosynthetic motif. The repetitive structure presents challenges both for synthesis and for structural characterization. In this synthesis of the (Z8,E2,ω)-undecaprenol of prokaryotic glycobiology, we exemplify solutions to these challenges. Allylation of sulfone-derived carbanions controlled the stereochemistry, and its proof-of-structure was secured by Eu(hfc)3 complexation to disperse the overlaid resonances of its 1H NMR spectrum.

Graphical abstract: Synthesis and shift-reagent-assisted full NMR assignment of bacterial (Z8,E2,ω)-undecaprenol

Supplementary files

Article information

Article type
Communication
Submitted
29 Aug 2017
Accepted
07 Nov 2017
First published
07 Nov 2017

Chem. Commun., 2017,53, 12774-12777

Synthesis and shift-reagent-assisted full NMR assignment of bacterial (Z8,E2,ω)-undecaprenol

M. Lee, D. Hesek, J. Zajíček, J. F. Fisher and S. Mobashery, Chem. Commun., 2017, 53, 12774 DOI: 10.1039/C7CC06781J

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