Enzymatic formation of unnatural novel chalcone, stilbene, and benzophenone scaffolds by plant type III polyketide synthase.
A C(19) hexaketide stilbene and a C(21) heptaketide chalcone were synthesized by Aloe arborescens octaketide synthase (OKS), a plant-specific type III polyketide synthase (PKS). Remarkably, the C(21) chalcone-forming activity was dramatically increased in a structure-guided OKS N222G mutant that produces a C(20) decaketide SEK15 from 10 molecules of malonyl-CoA. The findings suggested further strategies for production of unnatural polyketides by combination of the precursor-directed biosynthesis and the structure-guided engineering of type III PKS.
Shi
She-Po
SP
School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan.
Wanibuchi
Kiyofumi
K
Morita
Hiroyuki
H
Endo
Kohei
K
Noguchi
Hiroshi
H
Abe
Ikuro
I
D000217:Acyltransferases / Q000378:metabolism*; D000504:Aloe / Q000201:enzymology* / Q000235:genetics; D001577:Benzophenones / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002599:Chalcone / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry
D001577:Benzophenones; D013267:Stilbenes; D002599:Chalcone; C047723:benzophenone; D000217:Acyltransferases; C020141:flavanone synthetase