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Directed Biosynthesis of Mitragynine Stereoisomers.

Carsten SchotteYindi JiangDagny GrzechThu-Thuy T DangLarissa C LaforestFrancisco LeónMarco MottinelliSatya Swathi NadakudutiChristopher R McCurdySarah Ellen O'connor
Published in: Journal of the American Chemical Society (2023)
Mitragyna speciosa ("kratom") is used as a natural remedy for pain and management of opioid dependence. The pharmacological properties of kratom have been linked to a complex mixture of monoterpene indole alkaloids, most notably mitragynine. Here, we report the central biosynthetic steps responsible for the scaffold formation of mitragynine and related corynanthe-type alkaloids. We illuminate the mechanistic basis by which the key stereogenic center of this scaffold is formed. These discoveries were leveraged for the enzymatic production of mitragynine, the C-20 epimer speciogynine, and fluorinated analogues.
Keyphrases
  • chronic pain
  • pain management
  • tissue engineering
  • hydrogen peroxide
  • neuropathic pain
  • nitric oxide
  • spinal cord injury
  • drug induced