gem-Diprenylation of Acylphloroglucinols by a Fungal Prenyltransferase of the Dimethylallyltryptophan Synthase Superfamily

Kang Zhou; Carsten Wunsch; Jungui Dai; Shu-Ming Li

doi:10.1021/acs.orglett.6b03594

gem-Diprenylation of Acylphloroglucinols by a Fungal Prenyltransferase of the Dimethylallyltryptophan Synthase Superfamily

Org Lett. 2017 Jan 20;19(2):388-391. doi: 10.1021/acs.orglett.6b03594. Epub 2016 Dec 28.

Authors

Kang Zhou¹, Carsten Wunsch¹, Jungui Dai², Shu-Ming Li¹

Affiliations

¹ Institut für Pharmazeutische Biologie und Biotechnologie, Philipps-Universität Marburg , Robert-Koch-Strasse 4, 35037 Marburg, Germany.
² State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College , Xian Nong Tan Street, Beijing 100050, China.

PMID: 28029789
DOI: 10.1021/acs.orglett.6b03594

Abstract

Aspergillus terreus aromatic prenyltransferase (AtaPT) catalyzes predominantly C-monoprenylation of acylphloroglucinols in the presence of different prenyl diphosphates. With dimethylallyl diphosphate (DMAPP) as prenyl donor, gem-diprenylated products 1D3, 2D3, and 3D3 were also detected. High conversion of 1D1 to 1D3, 2D1 to 2D3, and 3D1 to 3D3 was demonstrated by incubation with AtaPT and DMAPP. The first example of gem-diprenylation by a member of the dimethylallyltryptophan synthase superfamily is provided.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkyl and Aryl Transferases
Dimethylallyltranstransferase / metabolism*
Diphosphates
Molecular Structure
Substrate Specificity

Substances

Diphosphates
Alkyl and Aryl Transferases
Dimethylallyltranstransferase
tryptophan dimethylallyltransferase