Aza-tryptamine substrates in monoterpene indole alkaloid biosynthesis

Hyang-Yeol Lee, Nancy Yerkes, Sarah E. O'Connor

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)1225-1229
Number of pages5
JournalChemistry & Biology
Volume16
Issue number12
DOIs
Publication statusPublished - 24 Dec 2009

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