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N-(17-Phosphonooxylinolenoyl)glutamine and N-(17-phosphonooxylinoleoyl)glutamine from insect gut: the first backbone-phosphorylated fatty acid derivatives in nature

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2004

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Oldham, Neil J.
Boland, Wilhelm

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http://nbn-resolving.de/urn:nbn:de:bsz:352-155488
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https://doi.org/10.1021/jo035382g
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The Journal of Organic Chemistry. 2004, 69(4), pp. 1104-1109. ISSN 0022-3263. Available under: doi: 10.1021/jo035382g

Zusammenfassung

N-(17-Phosphonooxylinolenoyl)glutamine (1) and N-(17-phosphonooxylinoleoyl)glutamine (2) were isolated from the regurgitate of Spodoptora exigua and identified as the first natural alkyl chain-phosphorylated fatty acid derivatives. The compounds were characterized by HPLC-MS/MS and the assigned structures confirmed by synthesis via a dissymmetric bis-Wittig approach as the key reaction. Rearing of the larvae on a diet enriched with inorganic phosphate increased the amount of the phosphorylated N-acyl glutamines in the regurgitate.

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570 Biowissenschaften, Biologie

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ISO 690SPITELLER, Dieter, Neil J. OLDHAM, Wilhelm BOLAND, 2004. N-(17-Phosphonooxylinolenoyl)glutamine and N-(17-phosphonooxylinoleoyl)glutamine from insect gut: the first backbone-phosphorylated fatty acid derivatives in nature. In: The Journal of Organic Chemistry. 2004, 69(4), pp. 1104-1109. ISSN 0022-3263. Available under: doi: 10.1021/jo035382g
BibTex
@article{Spiteller2004-02-20N17Ph-15548,
  year={2004},
  doi={10.1021/jo035382g},
  title={N-(17-Phosphonooxylinolenoyl)glutamine and N-(17-phosphonooxylinoleoyl)glutamine from insect gut: the first backbone-phosphorylated fatty acid derivatives in nature},
  number={4},
  volume={69},
  issn={0022-3263},
  journal={The Journal of Organic Chemistry},
  pages={1104--1109},
  author={Spiteller, Dieter and Oldham, Neil J. and Boland, Wilhelm}
}
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