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NMR Spectra of Sarekensane and synthetic compounds of interest

ORCID
0000-0002-4810-324X
Affiliation/Institute
Institut für Organische Chemie
Schulz, Stefan;
GND
0009-0003-3944-520X
Affiliation/Institute
Institut für Organische Chemie
Möllerke, Anton;
Affiliation/Institute
Institut für Organische Chemie
Bello, Jan;
Affiliation/Institute
University of Oslo
Leinaas, Hans Petter

The raw NMR datasets for the natural product sarekensane and synthetic precoursors of interest.
These datasets form an addition to the Article "Cyclopropane Hydrocarbons from the Springtail Vertagopus sarekensis - a New Class of Cuticular Lipids from Arthropods" in the Journal of Natural Products.
The here presented NMR data was crucial for the structure elucidation elaborated in the article and provides evidence for the identity of the synthetic compounds.
The original article abstract:
The epicuticle of insects is usually coated with a complex mixture of hydrocarbons, primarily straight-chain and methyl-branched alkanes, and alkenes. We were interested in whether springtails (Collembola), a sister class of the insects, also use such compounds. We focused here on Vertagopus sarekensis, an abundant Isotomidae species in European high alpine regions, exhibiting coordinated group behavior and migration. This coordination, suggesting chemical communication, made the species interesting for our study on epicuticular hydrocarbons in springtails with different degrees of group behavior.
We isolated a single hydrocarbon from its surface, which is the major epicuticular lipid. The structure was deduced by NMR analysis and GC/MS including derivatization. Total synthesis confirmed the structure as cis,cis-3,4,13,14-bismethylene-24-methyldotriacontane (4, sarekensane). The GC/MS analyses of some other cyclopropane hydrocarbons also synthesized showed the close similarity of both mass spectra and gas chromatographic retention indices of alkenes and cyclopropanes. Therefore, analyses of cuticular alkenes must be performed with appropriate derivatization to distinguish these two types of cuticular hydrocarbons. Sarekensane (4) is the first non-terpenoid cuticular hydrocarbon from Collembola that is biosynthesized via the fatty acid pathway, as are insect hydrocarbons and contains unprecedented cyclopropane rings in the chain, not previously reported from arthropods.

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