Unknown

Dataset Information

0

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

altmetric image

Publications

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]

Similar Datasets

| S-EPMC9464250 | biostudies-literature
| S-EPMC2474460 | biostudies-literature
| S-EPMC7317620 | biostudies-literature
| S-EPMC5238941 | biostudies-literature
| S-EPMC8493801 | biostudies-literature
| S-EPMC6003104 | biostudies-literature
| S-EPMC4516820 | biostudies-literature
| S-EPMC1459402 | biostudies-literature
| S-EPMC3530497 | biostudies-literature
| S-EPMC7024260 | biostudies-literature