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Absolute configuration of volicitin, an elicitor of plant volatile biosynthesis from lepidopteran larvae

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2001

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Pohnert, Georg
Boland, Wilhelm

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http://nbn-resolving.de/urn:nbn:de:bsz:352-155577
DOI (zitierfähiger Link)
https://doi.org/10.1016/S0040-4039(00)02290-5
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Tetrahedron Letters. 2001, 42(8), pp. 1483-1485. ISSN 0040-4039. Available under: doi: 10.1016/S0040-4039(00)02290-5

Zusammenfassung

The absolute configuration of the hydroxylinolenoyl moiety of volicitin (17-hydroxylinolenoyl-l-glutamine) 1a/b from four lepidopteran larvae was determined by methanolysis and derivatisation of the resulting ester with (1R)-1-phenyl-ethylisocyanate 3. The absolute configuration of the resulting (1′R)-17-(1′-phenyl-ethylcarbamoyloxy)-methyl linolenoates 4a/b followed from GLC comparison with synthetic references. Natural volicitin 1 from caterpillars of Spodoptera exigua, S. frugiperda, S. littoralis and Heliothis virescens (Noctuidae) exhibits a high ee (92–96%) and has a 17S configuration.

Zusammenfassung in einer weiteren Sprache

Fachgebiet (DDC)
570 Biowissenschaften, Biologie

Schlagwörter

fatty acid amides, N-17-hydroxy-linolenoyl-l-glutamine, 1-phenyl-ethylisocyanate, stereochemistry

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ISO 690SPITELLER, Dieter, Georg POHNERT, Wilhelm BOLAND, 2001. Absolute configuration of volicitin, an elicitor of plant volatile biosynthesis from lepidopteran larvae. In: Tetrahedron Letters. 2001, 42(8), pp. 1483-1485. ISSN 0040-4039. Available under: doi: 10.1016/S0040-4039(00)02290-5
BibTex
@article{Spiteller2001Absol-15557,
  year={2001},
  doi={10.1016/S0040-4039(00)02290-5},
  title={Absolute configuration of volicitin, an elicitor of plant volatile biosynthesis from lepidopteran larvae},
  number={8},
  volume={42},
  issn={0040-4039},
  journal={Tetrahedron Letters},
  pages={1483--1485},
  author={Spiteller, Dieter and Pohnert, Georg and Boland, Wilhelm}
}
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