Publikation: Absolute configuration of volicitin, an elicitor of plant volatile biosynthesis from lepidopteran larvae
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2001
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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.
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Fachgebiet (DDC)
570 Biowissenschaften, Biologie
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fatty acid amides, N-17-hydroxy-linolenoyl-l-glutamine, 1-phenyl-ethylisocyanate, stereochemistry
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SPITELLER, 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)02290-5BibTex
@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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