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Issue 22, 2005
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New C16 fatty-acid-based oxylipin pathway in the marine diatom Thalassiosira rotula

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Abstract

An unprecedented series of C16 oxylipins (1–8) has been characterized from the marine diatom Thalassiosira rotula. Absolute stereochemistry of the major alcohols 2 and 3 was determined to be 9S by spectroscopic and chemical methods. All the described products are formally derived by unprecedented enzymatic oxidation of C16 fatty acids. Conversion of hexadeca-6,9,12-trienoic acid (C16:3 ω-4) into 3 unequivocally established the occurrence of (at least) a specific 9S-oxygenase activity. To the best of our knowledge, the present data reveal for the first time the existence of an organic network of oxygenase-mediated transformations that require C16 fatty acids as substrates in living cells.

Graphical abstract: New C16 fatty-acid-based oxylipin pathway in the marine diatom Thalassiosira rotula

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Article information


Submitted
25 Jul 2005
Accepted
13 Sep 2005
First published
06 Oct 2005

Org. Biomol. Chem., 2005,3, 4065-4070
Article type
Paper

New C16 fatty-acid-based oxylipin pathway in the marine diatom Thalassiosira rotula

G. d'Ippolito, A. Cutignano, R. Briante, F. Febbraio, G. Cimino and A. Fontana, Org. Biomol. Chem., 2005, 3, 4065
DOI: 10.1039/B510640K

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