ArticleJournal of the American Chemical Society2012
Synthesis and NMR characterization of (Z,Z,Z,Z,E,E,ω)-heptaprenol.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed, 12 citations in OpenAlex.
- Synthesis and shift-reagent-assisted full NMR assignment of bacterial (ZChemical communications (Cambridge, England) · 2017Article
- Reconstitution of peptidoglycan cross-linking leads to improved fluorescent probes of cell wall synthesis.Journal of the American Chemical Society · 2014Article
- Staphylococcus aureus Penicillin-Binding Protein 2 Can Use Depsi-Lipid II Derived from Vancomycin-Resistant Strains for Cell Wall Synthesis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2013Article
- Forming cross-linked peptidoglycan from synthetic gram-negative Lipid II.Journal of the American Chemical Society · 2013Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
We describe a practical, multigram synthesis of (2Z,6Z,10Z,14Z,18E,22E)-3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octacosaheptaen-1-ol [(Z(4),E(2),ω)-heptaprenol, 4] using the nerol-derived sulfone 8 as the key intermediate. Sulfone 8 is prepared by the literature route and is converted in five additional steps (18% yield from 8) to (Z(4),E(2),ω)-heptaprenol 4. The use of Eu(hfc)(3) as an NMR shift reagent not only enabled confirmation of the structure and stereochemistry of 4, but further enabled the structural assignment to a major side product from a failed synthetic connection. The availability by this synthesis of (Z(4),E(2),ω)-heptaprenol 4 in gram quantities will enable preparative access to key reagents for the study of the biosynthesis of the bacterial cell envelope.
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