Total Synthesis and Structure Confirmation of trans-Anhydromevalonate-5-phosphate, a Key Biosynthetic Intermediate of the Archaeal Mevalonate Pathway

Yoko Yasuno, Atsushi Nakayama, Kai Saito, Kohei Kitsuwa, Hironori Okamura, Mutsumi Komeyama, Hisashi Hemmi, Tetsuro Shinada

研究成果: Contribution to journalArticle査読

抄録

The mevalonate pathway is an upstream terpenoid biosynthetic route of terpenoids for providing the two five-carbon units, dimethylallyl diphosphate, and isopentenyl diphosphate. Recently, trans-anhydromevalonate-5-phosphate (tAHMP) was isolated as a new biosynthetic intermediate of the archaeal mevalonate pathway. In this study, we would like to report the first synthesis of tAHMP and its enzymatic transformation using one of the key enzymes, mevalonate-5-phosphate dehydratase from a hyperthermophilic archaeon, Aeropyrum pernix. Starting from methyl tetrolate, a Cu-catalyzed allylation provided an E-trisubstituted olefin in a stereoselective manner. The resulting E-olefin was transformed to tAHMP by cleavage of the olefin and phosphorylation. The structure of the synthetic tAHMP was unambiguously determined by NOESY analysis.

本文言語英語
ページ(範囲)2749-2754
ページ数6
ジャーナルJournal of Natural Products
84
10
DOI
出版ステータス出版済み - 10 22 2021
外部発表はい

All Science Journal Classification (ASJC) codes

  • 分析化学
  • 分子医療
  • 薬理学
  • 薬科学
  • 創薬
  • 補完代替医療
  • 有機化学

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