Recent Advances in Acyltransferase Domain of Type I Polyktide Synthases

doi:10.6023/cjoc201806016

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (9): 2377-2385.DOI: 10.6023/cjoc201806016 Previous Articles Next Articles

Special Issue: 合成科学

Reviews

I型聚酮合酶中酰基转移酶结构域的研究进展

沈洁洁^a,b, 毛旭明^a,b, 陈新爱^a,b, 李永泉^a,b

a 浙江大学药物生物技术研究所杭州 310058;
b 浙江省微生物生化与代谢工程重点实验室杭州 310058

收稿日期:2018-06-12 修回日期:2018-06-29 发布日期:2018-07-16
通讯作者: 李永泉 E-mail:lyq@zju.edu.cn
基金资助:
国家自然科学基金（Nos.3173002，31520103901，31470212，31571284）资助项目.

Recent Advances in Acyltransferase Domain of Type I Polyktide Synthases

Shen Jiejie^a,b, Mao Xuming^a,b, Chen Xin'ai^a,b, Li Yongquan^a,b

a Institute of Pharmaceutical Biotechnology, Zhejiang University, Hangzhou 310058;
b Key Laboratory of Microbial Biochemistry and Metabolism Engineering of Zhejiang Province, Hangzhou 310058

Received:2018-06-12 Revised:2018-06-29 Published:2018-07-16
Contact: 10.6023/cjoc201806016 E-mail:lyq@zju.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 3173002, 31520103901, 31470212, 31571284).

Most polyketide natural compounds, such as antibiotics, antineoplastics and immunosuppressants, are produced by type I polyketide synthases (PKSs). Type I PKSs are composed of several catalytic modules, each of which contains iterative domains, such as acyltransferase (AT) domain, for one round of polyketide chain elongation. The recent advances on AT domains of type I PKS modules and analyzes their categories, the diverse acyl subunits they transfer, their catalytic mechanisms and their protein structures are summarized. Moreover, the recent progress in AT engineering (AT domains swaps, AT site-directed mutagenesis and trans-AT complementation) for new polyketide derivatives is summarized, to show that the substrate specificity of AT domains is one of the key factors on determining the diversity of polyketide backbones. These works have laid a theoretical foundation for the further development of novel polyketides with multi-functions and in high-yields by AT domain engineering.

Key words: AT domain, substrate specificity, catalytic mechanism, type I PKS, polyketide

Cite this article

Shen Jiejie, Mao Xuming, Chen Xin'ai, Li Yongquan. Recent Advances in Acyltransferase Domain of Type I Polyktide Synthases[J]. Chin. J. Org. Chem., 2018, 38(9): 2377-2385.

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References

[1] Dunn, B. J.; Khosla, C. J. R. Soc., Interface 2013, 10, 20130297.
[2] Shen, B. Curr. Opin. Chem. Biol. 2003, 7, 285.
[3] Demydchuk, Y.; Sun, Y.; Hong, H.; Staunton, J.; Spencer, J. B.; Leadlay, P. F. ChemBioChem 2008, 9, 1136.
[4] Khosla, C.; Tang, Y.; Chen, A. Y.; Schnarr, N. A.; Cane, D. E. Annu. Rev. Biochem. 2007, 76, 195.
[5] Bailey, C. B.; Pasman, M. E.; Keatinge-Clay, A. T. Chem. Commun. (Camb) 2016, 52, 792.
[6] Li, S.; Lu, C.; Chang, X.; Shen, Y. Appl. Microbiol. Biotechnol. 2016, 100, 2641.
[7] Luhavaya, H.; Williams, S. R.; Hong, H.; Gonzaga de Oliveira, L.; Leadlay, P. F. ChemBioChem 2014, 15, 2081.
[8] Liang, Z. X. Nat. Prod. Rep. 2010, 27, 499.
[9] Lanen, S. G. V.; Shen, B. Curr. Top. Med. Chem. 2008, 8, 448.
[10] Fu, L. F.; Tao, Y.; Jin, M. Y.; Jiang, H. Biotechnol. Lett. 2016, 38, 2015.
[11] Taguchi, C.; Taura, F.; Tamada, T.; Shoyama, Y.; Tanaka, H.; Shoyama, Y.; Kuroki, R.; Morimoto, S. Acta Crystallogr., Sect. F 2008, 64, 217.
[12] Yu, D. Y.; Xu, F. C.; Zeng, J.; Zhan, J. X. IUBMB Life 2012, 64, 285.
[13] Fang, W. J.; Wang, C. J.; He, Y.; Zhou, Y. L.; Peng, X. D.; Liu, S. K. Acta Pharmacol. Sin. 2018, 39, 59.
[14] Fischbach, M. A.; Walsh, C. T. Chem. Rev. 2006, 106, 3468.
[15] Kotowska, M.; Pawlik, K.; Smulczyk-Krawczyszyn, A.; Bar-tosz-Bechowski, H.; Kuczek, K. Appl. Environ. Microbiol. 2009, 75, 887.
[16] Musiol, E. M.; Weber, T. Med. Chem. Commun. 2012, 3, 871.
[17] Ye, Z.; Musiol, E. M.; Weber, T.; Williams, G. J. Chem. Biol. 2014, 21, 636.
[18] Wong, F. T.; Jin, X.; Mathews, I. I.; Cane, D. E.; Khosla, C. Biochemistry 2011, 50, 6539.
[19] Cheng, Y. Q.; Tang, G. L.; Shen, B. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 3149.
[20] Pan, G. H.; Xu, Z. R.; Guo, Z. K.; Hindra; Ma, M.; Yang, D.; Zhou, H.; Gansemans, Y.; Zhu, X. C.; Huang, Y.; Zhao, L. X.; Jiang, Y.; Cheng, J. H.; Nieuwerburgh F. V.; Suh, J. W.; Duan, Y. W.; Shen, B. Proc. Natl. Acad. Sci. U. S. A. 2017, 114, E11131.
[21] Helfrich, E. J. N.; Piel, J. Nat. Prod. Rep. 2016, 33, 231.
[22] Calderone, C. T.; Iwig, D. F.; Dorrestein, P. C.; Kelleher, N. L.; Walsh, C. T. Chem. Biol. 2007, 14, 835.
[23] Butcher, R. A.; Schroeder, F. C.; Fischbach, M. A.; Straight, P. D.; Kolter, R.; Walsh, C. T.; Clardy, J. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 1506.
[24] Yadav, G.; Gokhale, R. S.; Mohanty, D. J. Mol. Biol. 2003, 328, 335.
[25] Jiang, C.; Qi, Z.; Kang, Q.; Liu, J.; Jiang, M.; Bai, L. Angew. Chem., Int. Ed. 2015, 54, 9097.
[26] Luzhetskyy, A.; Mayer, A.; Hoffmann, J.; Pelzer, S.; Holzenkamper, M.; Schmitt, B.; Wohlert, S. E.; Vente, A.; Bechthold, A. ChemBio-Chem 2007, 8, 599.
[27] Blauenburg, B.; Oja, T.; Klika, K. D.; Metsa-Ketela, M. ACS Chem. Biol. 2013, 8, 2377.
[28] Xu, Z.; Schenk, A.; Hertweck, C. J. Am. Chem. Soc. 2007, 129, 6022.
[29] Lowden, P. A.; Wilkinson, B.; Böhm, G. A.; Handa, S.; Floss, H. G.; Leadlay, P. F.; Staunton, J. Angew. Chem., Int. Ed. 2001, 40, 777.
[30] Paiva, N. L.; Roberts, M. F.; Demain, A. L. J. Ind. Microbiol. 1993, 12, 423.
[31] Mo, S.; Kim, D. H.; Lee, J. H.; Park, J. W.; Basnet, D. B.; Ban, Y. H.; Yoo, Y. J.; Chen, S. W.; Park, S. R.; Choi, E. A.; Kim, E.; Jin, Y. Y.; Lee, S. K.; Park, J. Y.; Liu, Y.; Lee, M. O.; Lee, K. S.; Kim, S. J.; Kim, D.; Park, B. C.; Lee, S. G.; Kwon, H. J.; Suh, J. W.; Moore, B. S.; Lim, S. K.; Yoon, Y. J. J. Am. Chem. Soc. 2011, 133, 976.
[32] Kato, Y.; Bai, L. Q.; Xue, Q.; Revill, W. P.; Yu, T. W.; Floss, H. G. J. Am. Chem. Soc. 2002, 124, 5268.
[33] Xia, M. L.; Huang, D.; Li, S. S.; Wen, J. P.; Jia, X. Q.; Chen Y. Biotechnol. Bioeng. 2013, 110, 2717.
[34] Goranovic, D.; Kosec, G.; Mrak, P.; Fujs, S.; Horvat, J.; Kuscer, E.; Kopitar, G.; Petkovic, H. J. Biol. Chem. 2010, 285, 14292.
[35] Dunn, B. J.; Cane, D. E.; Khosla, C. Biochemistry 2013, 52, 1839.
[36] Marsden, A. F.; Caffrey, P.; Aparicio, J. F.; Loughran, M. S.; Staunton, J.; Leadlay, P. F. Science 1994, 263, 378.
[37] Tsai, S. C.; Lu, H.; Cane, D. E.; Khosla, C.; Stroud, R. M. Bio-chemistry 2002, 41, 12598.
[38] Reeves, C. D.; Murli, S.; Ashley, G. W.; Piagentini, M.; Hutchinson, C. R.; McDaniel, R. Biochemistry 2001, 40, 15464.
[39] Wang, Y. Y.; Bai, L. F.; Ran, X. X.; Jiang, X. H.; Wu, H.; Zhang, W.; Jin, M. Y.; Li, Y. Q.; Jiang, H. Protein Pept. Lett. 2015, 22, 2.
[40] Jiang, H.; Wang, Y. Y.; Guo, Y. Y.; Shen, J. J.; Zhang, X. S.; Luo, H. D.; Ren, X. X.; Jiang, X. H.; Li, Y. Q. FEBS J. 2015, 282, 2527.
[41] Liew, C. W.; Nilsson, M.; Chen, M. W.; Sun, H. H.; Cornvik, T.; Liang, Z. X.; Lescar, J. J. Biol. Chem. 2012, 287, 23203.
[42] Tang, Y.; Kim, C. Y.; Mathews, I. I.; Cane, D. E.; Khosla, C. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 11124.
[43] Tang, Y.; Chen, A. Y.; Kim, C. Y.; Cane, D. E.; Khosla, C. Chem Biol. 2007, 14, 931.
[44] Li, Y.; Zhang, W.; Zhang, H.; Tian, W. Y.; Wu, L.; Wang, S. W.; Zheng, M. M.; Zhang, J. R.; Sun, C. H.; Deng, Z. X.; Sun, Y. H.; Qu, X. H.; Zhou, J. H. Angew. Chem., Int. Ed. 2018, 10.1002/anie.201802805.
[45] Caffrey, P.; Lynch, S.; Flood, E.; Finnan, S.; Oliynyk, M. Chem. Biol. 2001, 8, 713.
[46] Feng, J. F.; Zhou, R. C.; Guo, X. T.; Zhang, Y. Mod. Agric. Sci. Technol. 2011, 3, 24(in Chinese). (冯建飞, 周日成, 郭兴庭, 张扬, 现代农业科技, 2011, 3, 24.)
[47] Barajas, J. F.; Blake-Hedges, J. M.; Bailey, C. B.; Curran, S.; Keasling, J. D. Synth. Syst. Biotechnol. 2017, 2, 147.
[48] Oliynyk, M.; Brown, M. J.; Cortes, J.; Staunton, J.; Leadlay, P. F. Chem. Biol. 1996, 3, 833.
[49] Stassi, D. L.; Kakavas, S. J.; Reynolds, K. A.; Gunawardana, G.; Swanson, S.; Zeidner, D.; Jackson, M.; Liu, H.; Buko, A.; Katz, L. Proc. Natl. Acad. Sci. U. S. A. 1998, 95, 7305.
[50] Patel, K.; Piagentini, M.; Rascher, A.; Tian, Z. Q.; Buchanan, G. O.; Regentin, R.; Hu, Z.; Hutchinson, C. R.; McDaniel, R. Chem. Biol. 2004, 11, 1625.
[51] Wong, F. T.; Jin, X.; Mathews, I. I.; Cane, D. E.; Khosla, C. Biochemistry 2011, 50, 6539.
[52] Mcdaniel, R.; Thamchaipenet, A.; Gustafsson, C.; Fu, H.; Betlach, M.; Betlach, M.; Ashley, G. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 1846.
[53] Yuzawa, S.; Deng, K.; Wang, G.; Baidoo, E. E.; Northen, T. R.; Adams, P. D.; Katz, L.; Keasling, J. D. ACS Synth. Biol. 2017, 6, 139.
[54] Hans, M.; Hornung, A.; Dziarnowski, A.; Cane, D. E.; Khosla, C. J. Am. Chem. Soc. 2003, 125, 5366.
[55] Koryakina, I.; Kasey, C.; McArthur, J. B.; Lowell, A. N.; Chemler, J. A.; Hansen, D. A.; Sherman, D. H.; Williams, G. ACS Chem. Biol. 2017, 12, 114.
[56] Petkovic, H.; Sandmann, A.; Challis, I. R.; Hecht, H. J.; Silakowski, B.; Low, L.; Beeston, N.; Kuscer, E.; Gar-cia-Bernardo, J.; Leadlay, P. F.; Kendrew, S. G.; Wilkinson, B.; Müller R. Org. Biomol. Chem. 2008, 6, 500.
[57] Vecchio, F. D.; Petkovic, H.; Kendrew, S. G.; Low, L.; Wilkinson, B.; Lill, R.; Cortés, J.; Rudd, B. A. M.; Staunton, J.; Leadlay, P. F. J. Ind. Microbiol. Biotechnol. 2003, 30, 489.
[58] Ruan, X. A.; Pereda, A.; Stassi, D.; Zeidner, D.; Summers, R. G.; Jackson, M.; Shivakumar, A.; Kakavas, S.; Staver, M. J.; Donadio, S.; Katz, L. J. Bacteriol. 1997, 179, 6416.
[59] Sundermann U.; Bravo-Rodriguez, K.; Klopries, S.; Kushnir, S.; Gomez, H.; Sanchez-Garcia, E.; Schulz, F. ACS. Chem. Biol. 2013, 8, 443.
[60] Klopries, S.; Sundermann U.; Schulz, F. Beilstein J. Org. Chem. 2013, 9, 664.
[61] Koryakina, I.; McArthur, J.; Randall, S.; Draelos, M. M.; Musiol, E. M.; Muddiman, D. C.; Weber, T.; Williams, G. J. ACS Chem. Biol. 2013, 8, 200.
[62] Dunn, B. J.; Watts, K. R.; Robbins. T.; Cane, D. E.; Khosla, C. Biochemistry 2014, 53, 379.
[63] Ad, O.; Thuronyi, B. W.; Chang, M. C. Proc. Natl. Acad. Sci. U. S. A. 2017, 114, 660.
[64] Wesener, S. R.; Potharla, V. Y.; Cheng, Y. Q. Appl. Environ. Microbiol. 2011, 77, 1501.
[65] Lopanik, N. B.; Shields, J. A.; Buchholz, T. J.; Rath, C. M.; Hothersall, J.; Haygood, M. G.; Hakansson, K.; Thomas, C. M.; Sherman, D. H. Chem. Biol. 2008, 15, 1175.

I型聚酮合酶中酰基转移酶结构域的研究进展

Recent Advances in Acyltransferase Domain of Type I Polyktide Synthases

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