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New azodyrecins identified by a genome mining-directed reactivity-based screening

Atina Rizkiya Choirunnisa, Kuga Arima, Yo Abe, Noritaka Kagaya, Kei Kudo, Hikaru Suenaga, Junko Hashimoto, Manabu Fujie, Noriyuki Satoh, Kazuo Shin-ya, Kenichi Matsuda and Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2022, 18, 1017–1025. https://doi.org/10.3762/bjoc.18.102

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Supporting Information File 1: Experimental procedures, characterization data (¹H, ¹³C NMR, and HRMS) and biochemical characterization of recombinant Ady1.
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New azodyrecins identified by a genome mining-directed reactivity-based screening

Atina Rizkiya Choirunnisa, Kuga Arima, Yo Abe, Noritaka Kagaya, Kei Kudo, Hikaru Suenaga, Junko Hashimoto, Manabu Fujie, Noriyuki Satoh, Kazuo Shin-ya, Kenichi Matsuda and Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2022, 18, 1017–1025. https://doi.org/10.3762/bjoc.18.102

How to Cite

Choirunnisa, A. R.; Arima, K.; Abe, Y.; Kagaya, N.; Kudo, K.; Suenaga, H.; Hashimoto, J.; Fujie, M.; Satoh, N.; Shin-ya, K.; Matsuda, K.; Wakimoto, T. Beilstein J. Org. Chem. 2022, 18, 1017–1025. doi:10.3762/bjoc.18.102

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TY  - JOUR
A1  - Choirunnisa, Atina Rizkiya
A1  - Arima, Kuga
A1  - Abe, Yo
A1  - Kagaya, Noritaka
A1  - Kudo, Kei
A1  - Suenaga, Hikaru
A1  - Hashimoto, Junko
A1  - Fujie, Manabu
A1  - Satoh, Noriyuki
A1  - Shin-ya, Kazuo
A1  - Matsuda, Kenichi
A1  - Wakimoto, Toshiyuki
T1  - New azodyrecins identified by a genome mining-directed reactivity-based screening
JF  - Beilstein Journal of Organic Chemistry
PY  - 2022///
VL  - 18
SP  - 1017
EP  - 1025
SN  - 1860-5397
DO  - 10.3762/bjoc.18.102
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.18.102
KW  - biosynthesis
KW  - methyltransferase
KW  - natural azoxides
KW  - reactivity-based screening
KW  - Streptomyces
N2  - Only a few azoxy natural products have been identified despite their intriguing biological activities. Azodyrecins D–G, four new analogs of aliphatic azoxides, were identified from two Streptomyces species by a reactivity-based screening that targets azoxy bonds. A biological activity evaluation demonstrated that the double bond in the alkyl side chain is important for the cytotoxicity of azodyrecins. An in vitro assay elucidated the tailoring step of azodyrecin biosynthesis, which is mediated by the S-adenosylmethionine (SAM)-dependent methyltransferase Ady1. This study paves the way for the targeted isolation of aliphatic azoxy natural products through a genome-mining approach and further investigations of their biosynthetic mechanisms.
ER  -

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Scholarly Works

Pfeifer, K.; Van Cura, D.; Wu, K. J. Y.; Balskus, E. P. Chemical capture of diazo metabolites reveals biosynthetic hydrazone oxidation. 2025. doi:10.1101/2025.05.24.655970
Angeli, C.; Atienza-Sanz, S.; Schröder, S.; Hein, A.; Li, Y.; Argyrou, A.; Osipyan, A.; Terholsen, H.; Schmidt, S. Recent Developments and Challenges in the Enzymatic Formation of Nitrogen-Nitrogen Bonds. ACS catalysis 2024, 15, 310–342. doi:10.1021/acscatal.4c05268
Matsuda, K.; Wakimoto, T. Bacterial Hydrazine Biosynthetic Pathways Featuring Cupin/Methionyl tRNA Synthetase-like Enzymes. Chembiochem : a European journal of chemical biology 2024, 25, e202300874. doi:10.1002/cbic.202300874
Maleckis, M.; Wibowo, M.; Gren, T.; Jarmusch, S. A.; Sterndorff, E. B.; Booth, T.; Henriksen, N. N. S. E.; Whitford, C. M.; Jiang, X.; Jørgensen, T. S.; Ding, L.; Weber, T. Biosynthesis of the Azoxy Compound Azodyrecin from Streptomyces mirabilis P8-A2. ACS chemical biology 2024, 19, 641–653. doi:10.1021/acschembio.3c00632
Shi, J.; Zang, X.; Zhao, Z.; Shen, Z.; Li, W.; Zhao, G.; Zhou, J.; Du, Y.-L. Conserved Enzymatic Cascade for Bacterial Azoxy Biosynthesis. Journal of the American Chemical Society 2023, 145, 27131–27139. doi:10.1021/jacs.3c12018
Maleckis, M.; Wibowo, M.; Gren, T.; Jarmusch, S. A.; Sterndorff, E. B.; Booth, T.; Henriksen, N. N. S. E.; Whitford, C. M.; Jiang, X.; Jørgensen, T. S.; Ding, L.; Weber, T. Biosynthesis of the azoxy compound azodyrecin fromStreptomyces mirabilisP8-A2. Cold Spring Harbor Laboratory 2023. doi:10.1101/2023.10.13.562208

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