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Aza-tryptamine substrates in monoterpene indole alkaloid biosynthesis.

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.

SUBMITTER: Lee HY

PROVIDER: S-EPMC2807416 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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Aza-tryptamine substrates in monoterpene indole alkaloid biosynthesis.

Lee Hyang-Yeol HY Yerkes Nancy N O'Connor Sarah E SE

Chemistry & biology 20091201 12

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-direct ...[more]

PMID: 20064432

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