Dearomative -diprenylation of Hydroxynaphthalenes by an Engineered Fungal Prenyltransferase

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 Oct 24

PMID 36276050

Authors

Yuanyuan Xu

Dan Li

Wenxuan Wang

Kangping Xu

Guishan Tan

Jing Li

Shu-Ming Li

Xia Yu

Affiliations

Soon will be listed here.

Abstract

Prenylation usually improves structural diversity and bioactivity in natural products. Unlike the discovered enzymatic -diprenylation of mono- and tri-cyclic aromatic systems, the enzymatic approach for -diprenylation of bi-cyclic hydroxynaphthalenes is new to science. Here we report an enzymatic example for dearomative C4 -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.

Citing Articles

A basidomycetous hydroxynaphthalene-prenylating enzyme exhibits promiscuity toward prenyl donors.

Martin A, Dierlamm N, Zocher G, Li S Appl Microbiol Biotechnol. 2023; 107(15):4845-4852.

PMID: 37326682 PMC: 10344970. DOI: 10.1007/s00253-023-12621-1.

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