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Verification of the versatility of the in vitro enzymatic reaction giving (+)-cis-12-Oxo-phytodienoic acid
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| Title: | Verification of the versatility of the in vitro enzymatic reaction giving (+)-cis-12-Oxo-phytodienoic acid |
| Authors: | Ito, Yusuke Browse this author | | Sasaki, Kento Browse this author | | Ogihara, Tsuyoshi Browse this author | | Kitaoka, Naoki Browse this author →KAKEN DB | | Takahahi, Kosaku Browse this author | | Matsuura, Hideyuki Browse this author →KAKEN DB |
| Issue Date: | 1-Oct-2021 |
| Publisher: | Elsevier |
| Journal Title: | Bioorganic & medicinal chemistry letters |
| Volume: | 49 |
| Start Page: | 128284 |
| Publisher DOI: | 10.1016/j.bmcl.2021.128284 |
| Abstract: | Jasmonic acid (JA) is a plant hormone involved in the defense response against insects and fungi. JA is synthesized from alpha-linolenic acid (LA) by the octadecanoid pathway in plants. 12-oxo-Phytodienoic acid (OPDA) is one of the biosynthetic intermediates in this pathway. The reported stereo selective total synthesis of cis-(+)-OPDA is not very efficient due to the many steps involved in the reaction as well as the use of water sensitive reactions. Therefore, we developed an enzymatic method for the synthesis of OPDA using acetone powder of flax seed and allene oxide cyclase (PpAOC2) from Physcomitrella patens. From this method, natural cis-(+)-OPDA can be synthesized in the high yield of approximately 40%. In this study, we investigated the substrate specificity of the enzymatic synthesis of other OPDA analogs with successions to afford OPDA amino acid conjugates, dinor-OPDA (dn-OPDA), and OPDA monoglyceride, and it was suggested that the biosynthetic pathway of arabidopsides could occur via MGDG. |
| Rights: | ©2021. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/ | | http://creativecommons.org/licenses/by-nc-nd/4.0/ |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/90436 |
| Appears in Collections: | 農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 松浦 英幸
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