Aza-Tryptamine Substrates in Monoterpene Indole Alkaloid Biosynthesis

作者：Lee Hyang Yeol; Yerkes Nancy; O'Connor Sarah E^*

来源：Chemistry & Biology, 2009, 16(12): 1225-1229.

DOI：10.1016/j.chembiol.2009.11.016

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.

• 出版日期2009-12-24