An Enzymatic Cyclopentyl[b]indole Formation Involved in Scytonemin Biosynthesis
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CitationBalskus, Emily P., and Christopher T. Walsh. 2009. “ An Enzymatic Cyclopentyl[ b ]indole Formation Involved in Scytonemin Biosynthesis .” Journal of the American Chemical Society 131 (41) (October 21): 14648–14649.
AbstractPrevious studies of the biosynthetic enzymes involved in the assembly of scytonemin (1), a cyanobacterial sunscreen, have identified β-ketoacid 2 as an important intermediate that is produced by ThDP-dependent enzyme ScyA. We now report that ScyC, previously annotated as a hypothetical protein, catalyzes cyclization and decarboxylation of 2 to generate ketone 5. Assembly of the cyclopentyl[b]indole structure in this manner has little precedent in the chemical literature. Additional mechanistic experiments have revealed that cyclization likely precedes decarboxylation and that the latter event may provide a driving force for cyclopentane formation.
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