title: Synthesis of (5Z,8Z,11Z,14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-3H8]-analogues through a common synthetic route.
abstract: Total synthesis of (5Z,8Z,11Z,14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-3H8]-analogues via the corresponding p-toluenesulphonates is reported. This synthetic approach allows the preparation of radioactively labelled arachidonic acid derivatives following a common synthetic route. Activity assays indicated that 15-lipoxygenases may tolerate the azido group in the substrate binding pocket and thus, radioactively labelled azido compounds may be used as photo-affinity probes to investigate mechanistic features of eicosanoid biosynthesis.
authors.affiliation: M.V. Lomonosov State Academy of Fine Chemical Technology, Moscow, Russia.
authors.forename: Stepan G
authors.initials: SG
authors.lastname: Romanov
authors.forename: Igor V
authors.initials: IV
authors.lastname: Ivanov
authors.forename: Valery P
authors.initials: VP
authors.lastname: Shevchenko
authors.forename: Igor Yu
authors.initials: IY
authors.lastname: Nagaev
authors.forename: Alexandr A
authors.initials: AA
authors.lastname: Pushkov
authors.forename: Nikolai F
authors.initials: NF
authors.lastname: Myasoedov
authors.forename: Galina I
authors.initials: GI
authors.lastname: Myagkova
authors.forename: Hartmut
authors.initials: H
authors.lastname: Kuhn
mesh_terms: D000818:Animals; D001093:Arachidonate 15-Lipoxygenase / Q000378:metabolism; D016718:Arachidonic Acid / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D007700:Kinetics; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011817:Rabbits; D012156:Reticulocytes / Q000201:enzymology; D013025:Glycine max / Q000201:enzymology
chemical_list: D016718:Arachidonic Acid; D001093:Arachidonate 15-Lipoxygenase