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Issue 19, 2017
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Molecular and genetic basis for early stage structural diversifications in hapalindole-type alkaloid biogenesis

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Abstract

Heterologous expressions and purifications of all WelU proteins from the welwitindolinone pathways in Hapalosiphon welwitschii UTEX B1830 and IC-52-3 led to the discovery that WelU1 and WelU3 selectively assemble 12-epi-fischerindole U (2) and 12-epi-hapalindole C (1), respectively, from 3-geranyl 3-isocyanovinyl indolenine (4) via an enzymatic cascade featuring the Cope rearrangement, stereoselective aza-Prins cyclization and regioselective carbocation deposition. In combination with the in vitro characterization of WelU1/WelU3-homolog AmbU4 for the biogenesis of 12-epi-hapalindole U, this study provide a unified view on the origin of the early stage structural diversifications in hapalindole-type alkaloid biosynthesis, post common intermediate 4.

Graphical abstract: Molecular and genetic basis for early stage structural diversifications in hapalindole-type alkaloid biogenesis

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Publication details

The article was received on 30 Jan 2017, accepted on 15 Feb 2017 and first published on 15 Feb 2017


Article type: Communication
DOI: 10.1039/C7CC00782E
Citation: Chem. Commun., 2017,53, 2826-2829
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    Molecular and genetic basis for early stage structural diversifications in hapalindole-type alkaloid biogenesis

    Q. Zhu and X. Liu, Chem. Commun., 2017, 53, 2826
    DOI: 10.1039/C7CC00782E

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