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Updated: Apr 28, 2026

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

Published on: October 4, 2019

Propellane Alkaloid Biosynthesis and Total Synthesis via Interrupted Reaction Pathways.

John M Billingsley¹, Jiaming Ding², Allison T Hands²

¹Department of Chemical and Biomolecular Engineering, University of California, Los Angeles, California 90095, United States.

ACS Central Science

|April 27, 2026

Summary

This summary is machine-generated.

This study reveals the biosynthesis and total synthesis of subrubine alkaloids, a new family of microbial compounds. Interrupted reaction pathways are key to constructing their complex diaza[3.3.3]-propellane structures.

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Area of Science:

Natural Product Biosynthesis
Organic Synthesis
Chemical Biology

Background:

Interrupted reactions offer novel strategies for complex natural product synthesis.
Microbial natural products often possess unique and complex chemical scaffolds.
Pyrrolidinoindoline alkaloids represent a class of compounds with diverse biological activities.

Purpose of the Study:

To elucidate the biosynthesis of the newly discovered subrubine alkaloid family.
To achieve the total synthesis of pensubrubine, a representative subrubine.
To explore the utility of interrupted reaction pathways in natural product assembly.

Main Methods:

High-resolution genome mining to identify novel natural product pathways.
Complete pathway reconstitution to confirm enzyme function.
Concise total synthesis employing interrupted Fischer indolization.

Main Results:

Discovery and characterization of the subrubine alkaloid family, featuring microbial diaza[3.3.3]-propellane pyrrolidinoindolines.
Identification of SubF as a propellane synthase directing biosynthesis via intramolecular Mannich cyclization.
Development of a 7-step total synthesis of pensubrubine, establishing its absolute configuration.

Conclusions:

Interrupted pathways are valuable for constructing complex molecular architectures like subrubines.
The findings expand the known chemical diversity of microbial alkaloids.
This work provides a foundation for accessing and studying subrubine natural products.