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

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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

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Publication details

The article was received on 29 Aug 2017, accepted on 07 Nov 2017 and first published on 07 Nov 2017


Article type: Communication
DOI: 10.1039/C7CC06781J
Citation: Chem. Commun., 2017, Advance Article
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    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, Advance Article , DOI: 10.1039/C7CC06781J

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