The formation of C-C bonds in an enantioselective fashion to create complex polycyclic scaffolds in the hapalindole/fischerindole type alkaloids represents a compelling and urgent challenge in microbial biosynthesis. Here we determine the biochemical and structural basis for tri-/tetracyclic core formation in these secondary metabolites, involving a new class of proteins that catalyze a complex cyclization cascade. Li, S., Lowell, A. N., Yu, F., Raveh, A., Newmister, S. A., Bair, N., Schaub, J. M., Williams, R. M. and Sherman, D. H. 2015. Hapalindole/ambiguine biogenesis is mediated by a Cope re-arrangement, C-C bond-forming cascade. J. Amer. Chem. Soc. 137(49):15366-153699. doi: 10.1021/jacs.5b10136. PMCID:PMC4681624 Li, S., Lowell, A. N., Yu, F., Newmister, S. A., Williams, R. M. and Sherman, D. H. 2017. Decoding cyclase-dependent assembly of hapalindole and fischerindole alkaloids. 2017 Mar 13. doi: 10.1038/nchembio.2327. [Epub ahead of print]

Function and structure of a new class of indole alkaloid cyclases in the Stigonematales cyanobacteria

254th National Meeting (2017)

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