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 (Z,E,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) complexation to disperse the overlaid resonances of its H NMR spectrum.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5749266 | PMC |
| http://dx.doi.org/10.1039/c7cc06781j | DOI Listing |
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Synthesis and shift-reagent-assisted full NMR assignment of bacterial (Z,E,ω)-undecaprenol.
Chem Commun (Camb)
November 2017
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
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 (Z,E,ω)-undecaprenol of prokaryotic glycobiology, we exemplify solutions to these challenges.
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