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

Kwo-Kwang Abraham Wang, Tai L. Ng, Peng Wang, Zedu Huang, View ORCID ProfileEmily P. Balskus, View ORCID ProfileWilfred A. van der Donk
doi: https://doi.org/10.1101/365031
Kwo-Kwang Abraham Wang
1Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois, USA
2Carl R. Woese Institute for Genomic Biology, University of Illinois at Urbana-Champaign, Urbana, Illinois, USA
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Tai L. Ng
3Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts, USA
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Peng Wang
3Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts, USA
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Zedu Huang
1Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois, USA
2Carl R. Woese Institute for Genomic Biology, University of Illinois at Urbana-Champaign, Urbana, Illinois, USA
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Emily P. Balskus
3Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts, USA
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  • For correspondence: balskus@chemistry.harvard.edu vddonk@illinois.edu
Wilfred A. van der Donk
1Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois, USA
2Carl R. Woese Institute for Genomic Biology, University of Illinois at Urbana-Champaign, Urbana, Illinois, USA
4Howard Hughes Medical Institute
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  • For correspondence: balskus@chemistry.harvard.edu vddonk@illinois.edu
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Abstract

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 NN 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.

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Posted July 09, 2018.
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Glutamic acid is a carrier for hydrazine during the biosyntheses of fosfazinomycin and kinamycin
Kwo-Kwang Abraham Wang, Tai L. Ng, Peng Wang, Zedu Huang, Emily P. Balskus, Wilfred A. van der Donk
bioRxiv 365031; doi: https://doi.org/10.1101/365031
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Glutamic acid is a carrier for hydrazine during the biosyntheses of fosfazinomycin and kinamycin
Kwo-Kwang Abraham Wang, Tai L. Ng, Peng Wang, Zedu Huang, Emily P. Balskus, Wilfred A. van der Donk
bioRxiv 365031; doi: https://doi.org/10.1101/365031

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