Enzymatic synthesis of bis-5-alkylresorcinols by resorcinol-producing type III polyketide synthases.
No enzyme systems responsible for the biosynthesis of structurally and biosynthetically intriguing bis-5-alkylresorcinols produced by plants have been identified. Herein, we show that bacterial, fungal and plant alkylresorcinol-producing type III polyketide synthases (PKSs), such as ArsB in the Gram-negative bacterium Azotobacter vinelandii, ORAS in the fungus Neurospora crassa and ARAS2 in the rice plant Oryza sativa, can synthesize bis-5-alkylresorcinol from alkanedioic acid N-acetylcysteamine dithioester as a starter substrate and from malonyl-CoA as an extender substrate by two-step conversion. Plants presumably use a type III PKS for the biosynthesis of bis-5-alkylresorcinols.
Miyanaga
Akimasa
A
Department of Biotechnology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Tokyo, Japan.
Horinouchi
Sueharu
S
D000217:Acyltransferases / Q000737:chemistry* / Q000235:genetics; D000478:Alkylation; D002264:Carboxylic Acids / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D007527:Isoenzymes / Q000235:genetics / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008316:Malonyl Coenzyme A / Q000378:metabolism; D013058:Mass Spectrometry; D011994:Recombinant Proteins / Q000378:metabolism; D012118:Resorcinols / Q000138:chemical synthesis*; D013056:Spectrophotometry, Ultraviolet; D013379:Substrate Specificity
D002264:Carboxylic Acids; D007527:Isoenzymes; D011994:Recombinant Proteins; D012118:Resorcinols; D008316:Malonyl Coenzyme A; D000217:Acyltransferases; C020141:flavanone synthetase