Biomimetic synthesis of a new class of bacterial signaling molecules.
The first synthesis of a newly discovered class of bacterial signaling molecules from Streptomyces coelicolor has been developed. These molecules, known as the methylenomycin furans (MMFs), trigger production of the antibiotic methylenomycin. The synthesis features a scandium triflate-catalyzed domino reaction of beta-ketoesters and dihydroxyacetone yielding 2,3,4-substituted furans. The proposed reaction sequence (aldol reaction, cyclization, and dehydrative aromatization) may be reminiscent of the biosynthetic reaction in which dihydroxyacetone phosphate and a beta-ketothioester are condensed by an enzyme.
Davis
Jesse B
JB
Department of Chemistry, Brown University, 324 Brook Street, Providence, Rhode Island 02912, USA.
Bailey
J Daniel
JD
Sello
Jason K
JK
D032701:Biomimetics; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D012538:Scandium / Q000737:chemistry*; D048372:Streptomyces coelicolor / Q000737:chemistry* / Q000378:metabolism
D005663:Furans; D008698:Mesylates; C436603:scandium triflate; D012538:Scandium