Identification of Genes Essential for Sulfamate and Fluorine Incorporation During Nucleocidin Biosynthesis.
biosynthesis
fluorine
gene disruption
nucleocidin
sulfamate
Journal
Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Titre abrégé: Chembiochem
Pays: Germany
ID NLM: 100937360
Informations de publication
Date de publication:
03 08 2022
03 08 2022
Historique:
revised:
05
05
2022
received:
10
03
2022
pubmed:
12
5
2022
medline:
6
8
2022
entrez:
11
5
2022
Statut:
ppublish
Résumé
Nucleocidin is an adenosine derivative containing 4'-fluoro and 5'-O-sulfamoyl substituents. In this study, nucleocidin biosynthesis is examined in two newly discovered producers, Streptomyces virens B-24331 and Streptomyces aureorectus B-24301, which produce nucleocidin and related derivatives at titers 30-fold greater than S. calvus. This enabled the identification of two new O-acetylated nucleocidin derivatives, and a potential glycosyl-O-acetyltransferase. Disruption of nucJ, nucG, and nucI, within S. virens B-24331, specifying a radical SAM/Fe-S dependent enzyme, sulfatase, and arylsulfatase, respectively, led to loss of 5'-O-sulfamoyl biosynthesis, but not fluoronucleoside production. Disruption of nucN, nucK, and nucO specifying an amidinotransferase, and two sulfotransferases respectively, led to loss of fluoronucleoside production. Identification of S. virens B-24331 as a genetically tractable and high producing strain sets the stage for understanding nucleocidin biosynthesis and highlights the utility of using 16S-RNA sequences to identify alternative producers of valuable compounds in the absence of genome sequence data.
Identifiants
pubmed: 35544615
doi: 10.1002/cbic.202200140
doi:
Substances chimiques
Sulfonic Acids
0
Fluorine
284SYP0193
sulfamic acid
9NFU33906Q
Sulfatases
EC 3.1.6.-
nucleocidin
F5097NG7JT
Adenosine
K72T3FS567
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200140Informations de copyright
© 2022 Wiley-VCH GmbH.
Références
J. Wang, M. Sánchez-Roselló, J. L. Aceña, C. del Pozo, A. E. Sorochinsky, S. Fustero, V. A. Soloshonok, H. Liu, Chem. Rev. 2014, 114, 2432-2506.
E. P. Gillis, K. J. Eastman, M. D. Hill, D. J. Donnelly, N. A. Meanwell, J. Med. Chem. 2015, 58, 8315-8359.
D. O′Hagan, Chem. Soc. Rev. 2008, 37, 308-319.
D. O′Hagan, H. Deng, Chem. Rev. 2015, 115, 634-649.
L. Ma, A. Bartholome, M. H. Tong, Z. Qin, Y. Yu, T. Shepherd, K. Kyeremeh, H. Deng, D. O′Hagan, Chem. Sci. 2015, 6, 1414-1419.
G. Gribble, in The Handbook of Environmental Chemistry (Ed.: A. H. Neilson), Springer, 2002, pp. 121-136.
J. Latham, E. Brandenburger, S. A. Shepherd, B. R. K. Menon, J. Micklefield, Chem. Rev. 2017, 118, 232-269.
S. J. Williams, S. G. Withers, Carbohydr. Res. 2000, 327, 27-46.
K. Isono, M. Uramoto, H. Kusakabe, N. Miyata, T. Koyama, M. Ubukata, S. K. Sethi, J. A. McCloskey, J. Antibiot. 1984, 37, 670.
J. J. Petkowski, W. Bains, S. Seager, J. Nat. Prod. 2018, 81, 423-446.
P. Mujumdar, S.-A. Poulsen, J. Nat. Prod. 2015, 78, 1470-1477.
T. Awakawa, L. Barra, I. Abe, J. Ind. Microbiol. Biotechnol. 2021, 48, kuab001.
Z. Hu, T. Awakawa, Z. Ma, I. Abe, Nat .Comms. 2019, 10, 184.
P. Van de Vijver, G. H. M. Vondenhoff, S. Denivelle, J. Rozenski, J. Verhaegen, A. Van Aerschot, P. Herdewijn, Bioorg. Med. Chem. Lett. 2009, 17, 260-269.
S. S. Dixit, R. S. Upadhayaya, J. Chattopadhyaya, Org. Biomol. Chem. 2012, 10, 6121.
M. C. Lux, L. C. Standke, D. S. Tan, J. Antibiot. 2019, 1-25.
J. Sourimant, C. M. Lieber, M. Aggarwal, R. M. Cox, J. D. Wolf, J.-J. Yoon, M. Toots, C. Ye, Z. Sticher, A. A. Kolykhalov, et al., Science 2022, 375, 161-167.
X. M. Zhu, S. Hackl, M. N. Thaker, L. Kalan, C. Weber, D. S. Urgast, E. M. Krupp, A. Brewer, S. Vanner, A. Szawiola, et al., ChemBioChem 2015, 16, 2498-2506.
X. Feng, D. Bello, P. T. Lowe, J. Clark, D. O′Hagan, Chem. Sci. 2019, 10, 9501-9505.
S. Zhang, D. Klementz, J. Zhu, R. Makitrynskyy, A. R. Ola Pasternak, S. Günther, D. L. Zechel, A. Bechthold, J. Biotechnol. 2019, 292, 23-31.
X. Feng, D. Bello, D. O′Hagan, RSC Adv. 2021, 11, 5291-5294.
X. Feng, N. Al Maharik, A. Bartholome, J. E. Janso, U. Reilly, D. O′Hagan, Org. Biomol. Chem. 2017, 15, 8006-8008.
U. Ngivprom, S. Kluaiphanngam, W. Ji, S. Siriwibool, A. Kamkaew, J. R. Ketudat Cairns, Q. Zhang, R.-Y. Lai, RSC Adv. 2021, 11, 3510-3515.
C. Zhao, J. Qi, W. Tao, L. He, W. Xu, J. Chan, Z. Deng, PLoS One 2014, 9, e114722.
J. Hug, C. Bader, M. Remškar, K. Cirnski, R. Müller, Antibiotics 2018, 7, 44-47.
S. Antoraz, R. I. Santamaría, M. Díaz, D. Sanz, H. Rodríguez, Front. Microbiol. 2015, 6, 461..
M. E. Rateb, Z. Yu, Y. Yan, D. Yang, T. Huang, S. Vodanovic-Jankovic, M. A. Kron, B. Shen, J. Antibiot. 2014, 67, 127-132.
H. B. Bode, B. Bethe, R. Höfs, A. Zeeck, ChemBioChem 2002, 3, 619-627.
N. Ziemert, M. Alanjary, T. Weber, Nat. Prod. Rep. 2016, 33, 988-1005.
Hindra, T. Huang, D. Yang, J. D. Rudolf, P. Xie, G. Xie, Q. Teng, J. R. Lohman, X. Zhu, Y. Huang, et al., J. Nat. Prod. 2014, 77, 2296-2303.
A. Hornung, M. Bertazzo, A. Dziarnowski, K. Schneider, K. Welzel, S.-E. Wohlert, M. Holzenkämpfer, G. J. Nicholson, A. Bechthold, R. D. Süssmuth, et al., ChemBioChem 2007, 8, 757-766.
X. Yan, Hindra, H. Ge, D. Yang, T. Huang, I. Crnovcic, C.-Y. Chang, S.-M. Fang, T. Annaval, X. Zhu, et al., J. Nat. Prod. 2018, 81, 594-599.
B. Shen, Hindra, X. Yan, T. Huang, H. Ge, D. Yang, Q. Teng, J. D. Rudolf, J. R. Lohman, Bioorg. Med. Chem. Lett. 2015, 25, 9-15.
Y. Chen, Q. Zhang, X. Feng, M. Wojnowska, D. O′Hagan, Org. Biomol. Chem. 2021, 19, 10081-10084.
M. Bernhardt, S. Berman, D. L. Zechel, A. Bechthold, ChemBioChem 2020, 21, 2659-2666.
S. Zhang, J. Zhu, D. L. Zechel, C. Jessen-Trefzer, R. T. Eastman, T. Paululat, A. Bechthold, ChemBioChem 2018, 19, 272-279.
L. Kalan, A. Gessner, M. N. Thaker, N. Waglechner, X. Zhu, A. Szawiola, A. Bechthold, G. D. Wright, D. L. Zechel, Chem. Biol. 2013, 20, 1214-1224.
R. E. Musso, I. Zabin, Biochemistry 1973, 12, 553-557.
A. P. Mehta, S. H. Abdelwahed, N. Mahanta, D. Fedoseyenko, B. Philmus, L. E. Cooper, Y. Liu, I. Jhulki, S. E. Ealick, T. P. Begley, J. Biol. Chem. 2015, 290, 3980-3986.
S. Lee, C. Uttamapinant, G. L. Verdine, Org. Lett. 2007, 9, 5007-5009.
I. D. Jenkins, J. P. Verheyden, J. G. Moffatt, J. Am. Chem. Soc. 1976, 98, 3346-3357.
V. Agarwal, Z. D. Miles, J. M. Winter, A. S. Eustáquio, A. A. El Gamal, B. S. Moore, Chem. Rev. 2017, 117, 5619-5674.
X. Feng, N. Al Maharik, A. Bartholome, J. E. Janso, U. Reilly, D. O′Hagan, Org. Biomol. Chem. 2017, 15, 8006-8008;
Angew. Chem. 2011, 123, 10077-10080.