title: Gram scale synthesis of specialized pro-resolving mediator 17(S)-HDHA using lipoxygenase enhanced by water-soluble reducing agent TCEP.
abstract: 17(S)-Hydroxy docosahexaenoic acid (17(S)-HDHA) is a specialized pro-resolving mediator. The oxidation of docosahexaenoic acid (DHA) to 17(S)-HDHA using soybean lipoxygenase was accomplished in the presence of the reducing agent TCEP in high yield and high enantio excess. We demonstrated application of this strategy to the synthesis of other fatty acids and to gram scale synthesis of 17(S)-HDHA.
authors.affiliation: Laboratory of Drug Design and Medicinal Chemistry, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan.
authors.forename: Toshimasa
authors.initials: T
authors.lastname: Itoh
authors.affiliation: Laboratory of Drug Design and Medicinal Chemistry, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan.
authors.forename: Tomoko
authors.initials: T
authors.lastname: Saito
authors.affiliation: Laboratory of Drug Design and Medicinal Chemistry, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan.
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Yamamoto
authors.affiliation: Laboratory of Drug Design and Medicinal Chemistry, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan.
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Ishida
authors.affiliation: Laboratory of Drug Design and Medicinal Chemistry, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan. Electronic address: yamamoto@ac.shoyaku.ac.jp.
authors.forename: Keiko
authors.initials: K
authors.lastname: Yamamoto
mesh_terms: D001894:Borohydrides / Q000737:chemistry; D004229:Dithiothreitol / Q000737:chemistry; D004281:Docosahexaenoic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D008042:Linolenic Acids / Q000737:chemistry; D008084:Lipoxygenase / Q000737:chemistry*; D010084:Oxidation-Reduction; D010720:Phosphines / Q000737:chemistry*; D017382:Reactive Oxygen Species / Q000737:chemistry; D012995:Solubility; D013025:Glycine max; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
chemical_list: D001894:Borohydrides; D004229:Dithiothreitol; D004281:Docosahexaenoic Acids; D008042:Linolenic Acids; D008084:Lipoxygenase; D010720:Phosphines; D017382:Reactive Oxygen Species; D014867:Water; C080938:tris(2-carboxyethyl)phosphine; C025364:sodium borohydride; C062894:17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid; C101084:lipoxygenase L-1
keywords: 17-HDHA; 17-HDoHE; Pro-resolving mediator; Resolvins D series; n-3 PUFA