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Journal Article

Aza-tryptamine substrates in monoterpene indole alkaloid biosynthesis

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Lee, H.-Y., Yerkes, N., & O'Connor, S. E. (2009). Aza-tryptamine substrates in monoterpene indole alkaloid biosynthesis. Chemistry & Biology, 16(12), 1225-1229. doi:10.1016/j.chembiol.2009.11.016.

Cite as: http://hdl.handle.net/21.11116/0000-0002-AB25-4
Biosynthetic pathways can be hijacked to yield novel compounds by introduction of novel starting materials. Here we have altered tryptamine, which serves as the starting substrate for a variety of alkaloid biosynthetic pathways, by replacing the indole with one of four aza-indole isomers. We show that two aza-tryptamine substrates can be successfully incorporated into the products of the monoterpene indole alkaloid pathway in Catharanthus roseus. Use of unnatural heterocycles in precursor-directed biosynthesis, in both microbial and plant natural product pathways, has not been widely demonstrated, and successful incorporation of starting substrate analogs containing the aza-indole functionality has not been previously reported. This work serves as a starting point to explore fermentation of aza-alkaloids from other tryptophan- and tryptamine-derived natural product pathways.