Issue 42, 2022

Dearomative gem-diprenylation of hydroxynaphthalenes by an engineered fungal prenyltransferase

Abstract

Prenylation usually improves structural diversity and bioactivity in natural products. Unlike the discovered enzymatic gem-diprenylation of mono- and tri-cyclic aromatic systems, the enzymatic approach for gem-diprenylation of bi-cyclic hydroxynaphthalenes is new to science. Here we report an enzymatic example for dearomative C4 gem-diprenylation of α-hydroxynaphthalenes, by the F253G mutant of a fungal prenyltransferase CdpC3PT. Experimental evidence suggests a sequential electrophilic substitution mechanism. We also explained the alteration of catalytic properties on CdpC3PT after mutation on F253 by modeling. This study provides a valuable addition to the synthetic toolkit for compound prenylation and it also contributes to the mechanistic study of prenylating enzymes.

Graphical abstract: Dearomative gem-diprenylation of hydroxynaphthalenes by an engineered fungal prenyltransferase

Supplementary files

Article information

Article type
Paper
Submitted
03 Aug 2022
Accepted
06 Sep 2022
First published
27 Sep 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 27550-27554

Dearomative gem-diprenylation of hydroxynaphthalenes by an engineered fungal prenyltransferase

Y. Xu, D. Li, W. Wang, K. Xu, G. Tan, J. Li, S. Li and X. Yu, RSC Adv., 2022, 12, 27550 DOI: 10.1039/D2RA04837J

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