4.8 Article

Identification of the Azaserine Biosynthetic Gene Cluster Implicates Hydrazine as an Intermediate to the Diazo Moiety

Journal

ORGANIC LETTERS
Volume 25, Issue 22, Pages 4061-4065

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c01229

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This study reports the biosynthetic gene cluster of Azaserine (1) from Glycomyces harbinensis and provides evidence from isotopic feeding, gene deletion, and biochemical experiments for a pathway involving hydrazinoacetic acid (2) and a peptidyl carrier protein-loaded serine (3) as intermediates to the final natural product 1.
Azaserine (1) is a natural product and nonproteinogenicamino acid containing a diazo group. Here we report the biosyntheticgene cluster for 1 from Glycomyces harbinensis. We then use isotopic feeding, gene deletion, and biochemical experimentsto support a pathway whereby hydrazinoacetic acid (2)and a peptidyl carrier protein-loaded serine (3) areintermediates on route to the final natural product 1.

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