Aza-Tryptamine Substrates in Monoterpene Indole Alkaloid Biosynthesis

Lee, H-Y, Yerkes, N and O'Connor, SE (2009) Aza-Tryptamine Substrates in Monoterpene Indole Alkaloid Biosynthesis. Chemistry & Biology, 16 (12). pp. 1225-1229. ISSN 1879-1301

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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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
University of East Anglia > Faculty of Science > Research Groups > Synthetic Chemistry
Related URLs:
Depositing User: Rhiannon Harvey
Date Deposited: 21 Mar 2012 14:17
Last Modified: 25 Jul 2018 04:36
URI: https://ueaeprints.uea.ac.uk/id/eprint/38407
DOI: 10.1016/j.chembiol.2009.11.016

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