期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 41, 页码 14648-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja906752u
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资金
- NIH [GM20011]
Previous studies of the biosynthetic enzymes involved in the assembly of scytonemin (1), a cyanobacterial sunscreen, have identified 8-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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