Gram scale synthesis of specialized pro-resolving mediator 17(S)-HDHA using lipoxygenase enhanced by water-soluble reducing agent TCEP

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• 作者：Toshimasa Itoh ; Tomoko Saito ; Yoshinori Yamamoto ; Hiroaki Ishida ; Keiko Yamamoto ; ^{yamamoto@ac.shoyaku.ac.jp" class="auth_mail" title="E-mail the corresponding author}
• 关键词：17-HDHA ; n-3 PUFA ; Pro-resolving mediator ; Resolvins D series ; 17-HDoHE
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2016
• 出版时间：15 January 2016
• 年：2016
• 卷：26
• 期：2
• 页码：343-345
• 全文大小：588 K

文摘

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.