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Glutamic acid is a carrier for hydrazine during the biosyntheses of fosfazinomycin and kinamycin
Glutamic acid is a carrier for hydrazine during the biosyntheses of fosfazinomycin and kinamycin
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Glutamic acid is a carrier for hydrazine during the biosyntheses of fosfazinomycin and kinamycin
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Glutamic acid is a carrier for hydrazine during the biosyntheses of fosfazinomycin and kinamycin
Glutamic acid is a carrier for hydrazine during the biosyntheses of fosfazinomycin and kinamycin
Journal Article

Glutamic acid is a carrier for hydrazine during the biosyntheses of fosfazinomycin and kinamycin

2018
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Overview
Fosfazinomycin and kinamycin are natural products that contain nitrogen–nitrogen (N–N) bonds but that are otherwise structurally unrelated. Despite their considerable structural differences, their biosynthetic gene clusters share a set of genes predicted to facilitate N–N bond formation. In this study, we show that for both compounds, one of the nitrogen atoms in the N–N bond originates from nitrous acid. Furthermore, we show that for both compounds, an acetylhydrazine biosynthetic synthon is generated first and then funneled via a glutamyl carrier into the respective biosynthetic pathways. Therefore, unlike other pathways to N–N bond-containing natural products wherein the N–N bond is formed directly on a biosynthetic intermediate, during the biosyntheses of fosfazinomycin, kinamycin, and related compounds, the N–N bond is made in an independent pathway that forms a branch of a convergent route to structurally complex natural products. The natural products fosfazinomycin A and kinamycin D are structurally distinct except for a nitrogen-nitrogen (N-N) bond. Here, the authors show that fosfazinomycin and kinamycin share a common pathway for N-N bond formation that is different from pathways found for other natural products.