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

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 conve...

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Published inOrganic letters Vol. 19; no. 2; pp. 388 - 391
Main Authors Zhou, Kang, Wunsch, Carsten, Dai, Jungui, Li, Shu-Ming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.01.2017
Amer Chemical Soc
Subjects
Alkyl and Aryl Transferases
Aspergillus terreus
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
Dimethylallyltranstransferase - metabolism
Diphosphates
fungi
Molecular Structure
organic compounds
Physical Sciences
Science & Technology
Substrate Specificity
POSITIONS
CATALYZES
POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOLS
BITTER ACIDS
BIOSYNTHESIS
PRENYLATION
ENZYMES
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.6b03594