Carboxylic acid derivativesCarboxylic acid derivatives Q 0510Conversion of Aryl Azides to O-Alkyl Imidates via Modified Staudinger Ligation.-In contrast to the related reaction of alkyl azides, which produces amide-linked compounds, the present process furnishes imidate-linked materials. This is considered to be a reflection of the steric and electronic differences between these classes of amides.-(RESTITUYO, J. A.; COMSTOCK, L. R.; PETERSEN, S. G.; STRINGFELLOW, T.; RAJSKI*, S. R.; Org. Lett. 5 (2003) 23, 4357-4360; Sch. Pharm., Univ. Wis., Madison, WI 53705, USA; Eng.) -Nuesgen 13-069

FK-228 is a potent histone deacetylase (HDAC) inhibitor with tremendous therapeutic potential against a wide array of human cancers. We describe the development of analogs that share FK-228's novel mechanism of activation and HDAC inhibition.

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The fatty acid composition of a Pseudomonas sp. (Alteromonas) and its host, the dinoflagellate Ostreopsis lenticularis, vectors in ciguatera fish poisoning, has been studied. The major fatty acids in O. lenticularis were 16:0, 20:5n-3, and 22:6n-3, but 18:2n-6, 18:3n-3, and 18:n-3 were also identified. In contrast to other dinoflagellates, 1 8:5n-3 was not detected in O. lenticularis. Even-chain fatty acids such as 9-16:1, 11-18:1, and 13-20:1 predominated in the Pseudomonas sp. from O. lenticularis, but 1 6-20% of (E)-11-methyl-12-octadecenoic acid was also identified. The chirality of the latter was confirmed by total synthesis (28% overall yield) starting from oxacyclotridecan-2-one. The fatty acid compositions of two other Pseudomonas species, from the palytoxin-producing zoanthids Palythoa mamillosa and P. caribdea, were also studied and were similar to that of the Pseudomonas sp. from O. lenticularis. The possibility of using some of these fatty acids as chemotaxonomic lipids in identifying marine animals that consume toxic dinoflagellates or zoanthids is discussed.

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