Aza-tryptamine substrates in monoterpene indole alkaloid biosynthesis

Lee, Hyang-Yeol, Yerkes, Nancy and O'Connor, Sarah E. (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
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017)
Depositing User:	Rhiannon Harvey
Date Deposited:	21 Mar 2012 14:17
Last Modified:	11 Mar 2024 00:41
URI:	https://ueaeprints.uea.ac.uk/id/eprint/38407
DOI:	10.1016/j.chembiol.2009.11.016

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