Aza-Tryptamine Substrates in Monoterpene Indole Alkaloid Biosynthesis
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Lee-2009-Aza-Tryptamine Subst.pdf
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Author(s)
Lee, Hyang-Yeol
Yerkes, Nancy Mary
O'Connor, Sarah Ellen
Yerkes, Nancy Mary
Date Issued
December 2009
Journal
Chemistry & Biology
Publisher
Elsevier B.V.
Citation
Lee, Hyang-Yeol, Nancy Yerkes, and Sarah E. O’Connor. “Aza-Tryptamine Substrates in Monoterpene Indole Alkaloid Biosynthesis.” Chemistry & Biology 16, no. 12 (December 2009): 1225–1229. © 2009 Elsevier Ltd.
Version
Final published version
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1016/j.chembiol.2009.11.016
