植物聚酮合酶在合成“非天然小分子”中的应用

doi:10.6023/cjoc201307012

有机化学 ›› 2013, Vol. 33 ›› Issue (12): 2469-2484.DOI: 10.6023/cjoc201307012 上一篇下一篇

综述与进展

植物聚酮合酶在合成“非天然小分子”中的应用

张乐^a, 王娟^a, 李彬^a, 高博闻^a, 王晓晖^a, 史社坡^a, 屠鹏飞^a,b

a 北京中医药大学中药现代研究中心北京 100029;
b 北京大学药学院天然药物及仿生药物国家重点实验室北京 100191

收稿日期:2013-07-12 修回日期:2013-08-08 发布日期:2013-08-21
通讯作者: 史社坡，屠鹏飞 E-mail:shishepo@163.com；pengfeitu@bjmu.edu.cn
基金资助:
教育部新世纪优秀人才支持计划(No. NCET-11-0604)、北京市自然科学基金(No. 5132022)资助项目.

Synthesis of Unnatural Small Molecules by Plant Specific Polyketide Synthases

Zhang Le^a, Wang Juan^a, Li Bin^a, Gao Bowen^a, Wang Xiaohui^a, Shi Shepo^a, Tu Pengfei^a,b

a Modern Research Center for Traditional Chinese Medicine, Beijing University of Chinese Medicine, Beijing 100029;
b State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191

Received:2013-07-12 Revised:2013-08-08 Published:2013-08-21
Supported by:
Project supported by the Trans-Century Training Program Foundation for the Talents of Humanities and Social Science by the State Education Commission (No. NCET-11-0604) and the Natural Science Foundation of Beijing (No. 5132022).

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摘要/Abstract

植物聚酮合酶催化起始底物(酰基辅酶A)反复地与丙二酰辅酶A进行缩合，通过C—C键的形成生成链状聚酮中间体，再经Claisen环合、Aldol环合等形式并经芳香化生成结构新颖多样的天然产物及“非天然小分子”. 对近年来发现的植物聚酮合酶的功能及来源、催化机制以及在合成“非天然小分子”中的应用进行综述.

关键词: 植物聚酮合酶, 非天然小分子, 组合合成, 组合生物合成

Plant polyketide synthases (PKSs) catalyze iterative decarboxylative condensations of malonyl units (Claisen-type C—C bond formation) with a CoA-linked starter molecule to produce linear chain polyketide intermediates. By Claisen, aldol cyclization, or lactonization, and aromatization, the linear chain polyketide intermediates produce varied unnatural small molecules. In this review, the functions of the known plant PKSs are summarized, and the catalytic mechanisms and applications of plant PKSs in the synthesis of unnatural small molecules are covered.

Key words: plant polyketide synthases, unnatural small molecules, combinatorial synthesis, combinatorial biosynthesis

引用此文

张乐, 王娟, 李彬, 高博闻, 王晓晖, 史社坡, 屠鹏飞. 植物聚酮合酶在合成“非天然小分子”中的应用[J]. 有机化学, 2013, 33(12): 2469-2484.

Zhang Le, Wang Juan, Li Bin, Gao Bowen, Wang Xiaohui, Shi Shepo, Tu Pengfei. Synthesis of Unnatural Small Molecules by Plant Specific Polyketide Synthases[J]. Chin. J. Org. Chem., 2013, 33(12): 2469-2484.

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参考文献

[1] (a) Rawlings, B. J. Nat. Prod. Rep. 2001, 18, 190.

(b) Rawlings, B. J. Nat. Prod. Rep. 2001, 18, 231.

(c) Keatinge-Clay, A. T. Nat. Prod. Rep. 2012, 29, 1050.

[2] (a) Zhang, W.; Tang, Y. Methods Enzymol.2009, 459, 367.

(b) Hertweck, C.; Luzhetskyy, A.; Rebets, Y.; Bechthold, A. Nat. Prod. Rep. 2007, 24, 162.

(c) Zhan, J. X. Curr. Top. Med. Chem. 2009, 9, 1598.

[3] (a) Abe, I.; Morita, H. Nat. Prod. Rep. 2010, 27, 809.

(b) Shi, S. P.; Morita, H.; Wanibuchi, K.; Mizuuchi, Y.; Noguchi, H.; Abe, I. Curr. Org. Synth. 2008, 5, 250.

(c) Austin, M. J.; Noel, J. P. Nat. Prod. Rep. 2003, 20, 79.

(d) Abe, I. Curr. Opin. Chem. Biol. 2012, 16, 179.

(e) Flores-Sanchez, I. J.; Verpoorte, R. Plant Physiol. Biochem. 2009, 47, 167.

[4] (a) Yu, D. Y.; Xu, F. C.; Zeng, J.; Zhan, J. X. IUBMB Life 2012, 64, 285.

(b) Li, S.; Crüschow, S.; Dordick, J. S.; Sherman, D. H. J. Biol. Chem. 2007, 282, 12765.

(c) Gross, F.; Luniak, N.; Perlova, O.; Gaitatzis, N.; Jenke-kodama, H.; Gerth, K.; Gottschalk, D.; Dittmann, E.; Müller, R. Arch. Microbiol. 2006, 185, 28.

(d) Zha, W.; Rubin-Pitel, S. B.; Zhao, H. J. Biol. Chem. 2006, 281, 32036.

(e) Tseng, C. C.; McLoughlin, S. M.; Kelleher, N. L.; Walsh, C. T. Biochemistry 2004, 43, 970.

[5] Reimold, U.; Kröger, M.; Kreuzaler, F.; Hahlbrock, K. EMBO J. 1983, 10, 1801.

[6] (a) Lukacin, R.; Springob, K.; Urbanke, C.; Schröder, G.; Matern, U. FEBS Lett. 1999, 448, 135.

(b) Junghanns, K. T.; Kneusel, R. E.; Gröger, D.; Matern, U. Phytochemistry 1998, 49, 403.

[7] Resmi, M. S.; Verma, P.; Gokhale, R. S.; Soniya, E. V. J. Biol. Chem. 2013,288, 7271.

[8] Shimokawa, Y.; Morita, H.; Abe, I. Front. Plant Sci.2012, 3, 1.

[9] Morita, H.; Shimokawa, Y.; Tanio, M.; Kato, R.; Noguchi, H.; Sugio, S.; Kohno, T.; Abe, I. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 669.

[10] Wakimoto, T.; Mori, T.; Morita, H.; Abe, I. J. Am. Chem. Soc. 2011, 133, 4746.

[11] Wanibuchi, K.; Zhang, P.; Abe, T.; Morita, H.; Kohno, T.; Chen, G. S.; Noguchi, H.; Abe, I. FEBS J. 2007, 274, 1073.

[12] (a) Mechoulam, R.; Ben-Shabat, S. Nat. Prod. Rep. 1999, 16, 131.

(b) Fellermerier, M.; Bacher, E. A.; Zenk, M. H. Eur. J. Biochem. 2001, 268, 1596.

[13] Taura, F.; Tanaka, S.; Taguch, C.; Fukamizu, T.; Tanaka, H.; Shoyama, Y.; Morimoto, S. FEBS Lett. 2009, 583, 2061.

[14] Gagne, S. J.; Stout, J. M.; Liu, E.; Boubakir, Z.; Clark, S. M.; Page, J. E. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 12811.

[15] (a) Koes, R. E.; Spelt, C. E.; van den Elzen, P. J. M.; Mol, J. N. M. Gene 1989, 81, 245.

(b) Abe, I.; Morita, H.; Nomura, A.; Noguchi, H. J. Am. Chem. Soc. 2000, 122, 11242.

(c) Ferrer, J. L.; Jez, J. M.; Bowman, M. E; Dixon, R. A.; Noel, J. P. Nat. Struct. Biol. 1999, 6, 775.

[16] (a) Schoppner, A.; Kindl, H. J. Biol. Chem. 1984, 259, 6806.

(b) Sparvoli, F.; Martin, C.; Scienza, A.; Gavazzi, G.; Tonelli, C. Plant Mol. Biol. 1994, 24, 743.

(c) Raiber, S.; Schröder, G.; Schröder, J. FEBS Lett. 1995, 361, 299.

(d) Schanz, S.; Schröder, G.; Schröder, J. FEBS Lett. 1992, 313, 71.

[17] (a) Dixon, R. A. Nature 2001, 411, 843.

(b) Roupe, K. A.; Remsberg, C. M.; Yáñez, J. A.; Davies, N. M. Curr. Clin. Pharmacol. 2006, 1, 81.

[18] Austin, M. B.; Bowman, M. E.; Ferrer, J.; Schröder, J.; Noel, J. P. Chem. Biol. 2004, 11, 1179.

[19] Eckermann, C.; Schröder, G.; Eckermann, S.; Strack, D.; Schmidt, J.; Schneider, B.; Schröder, J. Phytochemistry 2003, 62, 271.

[20] Preisig-Müller, R.; Gnau, P.; Kindl, H. Arch. Biochem. Biophys. 1995, 317, 201.

[21] Abe, I.; Oguro, S.; Utsumi, Y.; Sano, Y.; Noguchi, H. J. Am. Chem. Soc. 2005, 127, 12709.

[22] Abe, I.; Utsumi, Y.; Oguro, S.; Morita, H.; Sano, Y.; Noguchi, H. J. Am. Chem. Soc. 2005, 127, 1362.

[23] (a) Mizuuchi, Y.; Shi, S. P.; Wanibuchi, K.; Kojima, A.; Morita, H.; Abe, I. FEBS J. 2009, 276, 2391.

(b) Abe, I.; Utsumi, Y.; Oguro, S.; Noguchi, H. FEBS Lett. 2004, 562, 171.

(c) Abe, I.; Watanabe, T.; Lou, W.; Noguchi, H. FEBS J. 2006, 273, 208.

[24] (a) Prasanna, R.; Chandramoorthy, H. C.; Ramaiyapillai, P.; Sakthisekaran, D. Biomed. Prev. Nutr. 2011, 1, 153.

(b) Wei, X. C.; Du, Z. Y.; Zheng, X.; Cui, X. X.; Conney, A. H.; Zhang, K. Eur. J. Med. Chem. 2012, 53, 235.

(c) Rong, S.; Zhao, Y. T.; Bao, W.; Xiao, X.; Wang, D.; Nussler, A. K.; Yan, H.; Yao, P.; Liu, L. G. Phytomedicine 2012, 19, 545.

(d) Strasser, E. M.; Wessner, B.; Manhart, N.; Roth, E. Biochem. Pharmacol. 2005, 70, 552.

(e) Wei, Q. Y.; Chen, W. F.; Zhou, B.; Yang, L.; Liu, Z. L. Biochim. Biophys. Acta 2006, 1760, 70.

[25] Katsuyama, Y.; Kita, T.; Funa, N.; Horinouchi, S. J. Biol. Chem. 2009, 284, 11160.

[26] Katsuyama, Y.; Kita, T.; Horinouchi, S. FEBS Lett. 2009, 583, 2799.

[27] Katsuyama, Y.; Matsuzawa, M.; Funa, N.; Horinouchi, S. J. Biol. Chem. 2007, 282, 37702.

[28] (a) Nualkaew, N.; Morita, H.; Shimokawa, Y.; Kinjo, K.; Kushiro, T.; Wanchai, D.-E.; Ebizuka, Y.; Abe, I. Phytochemistry 2012, 77, 60.

(b) Liu, B.; Falkenstein-Paul, H.; Schmidt, W.; Beerhues, L. Plant J. 2003, 34, 847.

[29] Liu, B.; Beuerle, T.; Klundt, T.; Beerhues, L. Planta 2004, 218, 492.

[30] Eckermann, S.; Schröder, G.; Schmidt, J.; Strack, D.; Edrada, R. A.; Helariutta, Y.; Elomaa, P.; Kotilainen, M.; Kilpelalne, I.; Proksch, P.; Teeri, T. H.; Schröder, G. Nature 1998, 396, 387.

[31] (a) Okada, Y.; Ito, K. Biosci. Biotechnol. Biochem. 2001, 65, 150.

(b) Paniego, N. B.; Zuurbier, K. W. M.; Fung, S. Y.; Heijden, R. V.; Scheffer, J. J. C.; Verpoorte, R. Eur. J. Biochem. 1999, 262, 612.

[32] Ferrer, J.L.; Jez, J. M.; Bowman, M. E.; Dixon, R. A.; Noel, J. P. Nat. Struct. Biol. 1999, 6, 775.

[33] Jr, C. S.; Vickery, C. R.; Burkart, M. D.; Noel, J. P. Curr. Opin. Plant Biol. 2013, 16,1.

[34] Abe, I.; Morita, H.; Nomura, A.; Noguchi, H. J. Am. Chem. Soc. 2000, 122, 11242.

[35] Morita, H.; Yamashita, M.; Shi, S. P.; Wakimoto, T.; Kondoc, S.; Kato, R.; Sugio, S.; Kohno, T.; Abe, I. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 33.

[36] Karppinen, K.; Hokkanen, J.; Mattila, S.; Neubauer, P.; Hohtola, A. FEBS J. 2008, 275, 4329.

[37] (a) Abe, I.; Takahashi, Y.; Noguchi, H. Org. Lett. 2002, 4, 21.

(b) Abe, I.; Takahashi, Y.; Lou, W. W.; Noguchi, H. Org. Lett. 2003, 5, 8.

[38] Morita, H.; Kondo, S.; Oguro, S.; Noguchi, H.; Sugio, S.; Abe, I.; Kohno, T. Chem. Biol. 2007, 14, 359.

[39] (a) Abe, I.; Morita, H. Oguro, S.; Noma, H.; Wanibuchi, K.; Kawahara, N.; Goda, Y.; Noguchi, H.; Kohno, T. J. Am. Chem. Soc. 2007, 129, 5976.

(b) Shi, S. P.;Wanibuchi, K. Morita, H.;Endo, K.; Noguchi, H.; Abe, I. Org. Lett. 2009, 11, 551.

[40] Wanibuchi, K.; Morita, H.; Noguchi, H.; Abe, I. Bioorg. Med. Chem. Lett. 2011, 21, 2083.

[41] Kwon, S. J.; Lee, M.Y.; Ku, B.; Sherman, D. H.; Dordick, J .S. ACS Chem. Biol. 2007, 2, 419.

[42] (a) Hutchinson, C. R. Curr. Opin. Microbiol. 1998, 1, 319.

(b) Nielsen, J. Curr. Opin. Chem. Biol. 2002, 6, 297.

(c) Floss, H. G. J. Biotechnol. 2006, 124,242.

(d) Menzella, H. G.; Reeves, C. D. Curr. Opin. Microbiol. 2007, 10, 238.

[43] Katsuyama, Y.; Matsuzawa, M.; Nobutaka, F.; Horinouchi, S. Microbiology 2008, 154, 2620.

[44] (a) Watts, K. T.; Lee, P. C.; Schmidt-Dannert, C. BMC Biotechnol. 2006, 6, 22.

(b) Lim, C. G.; Fowler, Z. L.; Hueller, T.; Schaffer, S.; Koffas, M. A. Appl. Environ. Microbiol. 2011, 77, 3451.

[45] Katsuyama, Y.; Miyahisa, Y.; Nobutaka, F.; Horinouchi, S. Appl. Microbiol. Biotechnol. 2007, 73, 1143.

[46] Katsuyama, Y.; Nobutaka, F.; Miyahisa, I.; Sueharu, H. Chem. Biol. 2007, 14, 613.

植物聚酮合酶在合成“非天然小分子”中的应用

Synthesis of Unnatural Small Molecules by Plant Specific Polyketide Synthases

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