Citation: Zhang Jingxing, Yao Tingting, Liu Jing, Li Huayue, Li Wenli. Recent Advances in Cyclodipeptide Synthases-Dependent Biosynthetic Pathway[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 328-338. doi: 10.6023/cjoc201806003 shu

Recent Advances in Cyclodipeptide Synthases-Dependent Biosynthetic Pathway

Zhang Jingxing ^a ,
Yao Tingting ^a ,
Liu Jing ^a ,
Li Huayue ^a,b ,
Li Wenli ^a,b,,

a.
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003
b.
Laboratory for Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266237

Corresponding author: Li Wenli, liwenli@ouc.edu.cn
Received Date: 1 June 2018
Revised Date: 10 September 2018
Available Online: 17 February 2018
Fund Project: the National Natural Science Foundation of China 81561148012the National Natural Science Foundation of China 31171201the National Natural Science Foundation of China 31570032Project supported by the National Natural Science Foundation of China (Nos. 31171201, 81561148012, 31570032)

Figures(10)

Diketopiperazines (DKPs) are derivatives of cyclodipeptides resulted from the condensation of two α-amino acids. The conformationally constrained six-membered ring makes DKP an attractive pharmacophore in medicinal chemistry, exhibiting a wide range of bioactivities. Recently, there has been increased interests in synthesizing DKPs and biosynthesis is an effective pathway to broaden their structural diversity. Different from non-ribosomal peptide synthetases (NRPSs)-dependent pathways, cyclodipeptide synthases (CDPSs) use aminoacyl-tRNAs (aa-tRNAs) as substrates and the resulting cyclodipeptides are further modified by associated tailoring enzymes to yield the final products. To date, six CDPS-dependent pathways for synthesizing DKPs compounds have been reported. A brief overview of recent progresses on CDPS-dependent DKPs biosynthetic pathway is provided.
- diketopiperazines,
- non-ribosomal peptide synthetases,
- cyclodipeptide synthases,
- biosynthetic pathway
1. [1]
  Borthwick, A. D. Chem. Rev. 2012, 112, 3641. doi: 10.1021/cr200398y
2. [2]
  Giessen, T. W.; Marahiel, M. A. Int. J. Mol. Sci. 2014, 15, 14610. doi: 10.3390/ijms150814610
3. [3]
  Menegatti, S.; Hussain, M.; Naik, A. D. Biotechnol. Bioeng. 2013, 110, 857. doi: 10.1002/bit.24760
4. [4]
  de Carvalho, M. P.; Abraham, W. R. Curr. Med. Chem. 2012, 19, 3564. doi: 10.2174/092986712801323243
5. [5]
  Kohna, H.; Widger, W. Curr. Drug Targets: Infect. Disord. 2005, 5, 273. doi: 10.2174/1568005054880136
6. [6]
  Musetti, R.; Polizzotto, R.; Vecchione, A. Micron 2007, 38, 643. doi: 10.1016/j.micron.2006.09.001
7. [7]
  Ström, K.; Sjögren, J.; Broberg, A. Appl. Environ. Microbiol. 2002, 68, 4322. doi: 10.1128/AEM.68.9.4322-4327.2002
8. [8]
  Rodriguez, P. L.; Carrasco, L. J. Virol. 1992, 66, 1971.
9. [9]
  Kanoh, K.; Kohno, S.; Katada, J. Bull. Agric. Chem. Soc. Jpn. 1999, 63, 1130.
10. [10]
  Kanzaki, H.; Yanagisawa, S.; Nitoda, T. Bull. Agric. Chem. Soc. Jpn. 2004, 68, 2341.
11. [11]
  Waring, P.; Beaver, J. Gen. Pharmacol. 1996, 27, 1311. doi: 10.1016/S0306-3623(96)00083-3
12. [12]
  Cornacchia, C.; Cacciatore, I.; Baldassarre, L. Mini-Rev. Med. Chem. 2012, 12, 2. doi: 10.2174/138955712798868959
13. [13]
  Pérezpicaso, L.; Olivo, H. F.; Argotteramos, R. Bioorg. Med. Chem. Lett. 2012, 22, 7048. doi: 10.1016/j.bmcl.2012.09.094
14. [14]
  Bolognesi, M. L.; Ai, T. H.; Staderini, M. ChemMedChem 2010, 5, 1324. doi: 10.1002/cmdc.201000133
15. [15]
  Song, M. K.; Hwang, I. K.; Rosenthal, M. J. Exp. Biol. Med. 2003, 228, 1338. doi: 10.1177/153537020322801112
16. [16]
  Wang, G. X. Chin. J. Thromb. Hemostasis. 2011, 17, 234 (in Chinese). doi: 10.3969/j.issn.1009-6213.2011.05.014
17. [17]
  Sun, T. W.; Ding, Z. P.; Wang, S. X. Chin. J. Mar. Drug. 2016, 4, 79 (in Chinese).
18. [18]
  Martins, M. B.; Carvalho, I. Tetrahedron 2007, 63, 9923. doi: 10.1016/j.tet.2007.04.105
19. [19]
  Zhang, H.; Ning, X.; Hang, H. Org. Lett. 2013, 15, 5670. doi: 10.1021/ol4026556
20. [20]
  Wen, L.; Liu, Q. Q.; Yang, Q. H. Prog. Mod. Biomed. 2012, 119, 2894.
21. [21]
  Rajesh Shinghal, M. D.; Allison Barnes, M. S.; Mahar, K. M. J. Sex. Med. 2013, 10, 2506. doi: 10.1111/jsm.12272
22. [22]
  Charlton, P. A.; Faint, R. W.; Bent, F. Thromb. Haemostasis. 1996, 75, 808. doi: 10.1055/s-0038-1650371
23. [23]
  Park, D. K.; Lee, K. E.; Baek, C. H. J. Bacteriol. 2006, 188, 2214. doi: 10.1128/JB.188.6.2214-2221.2006
24. [24]
  (a) Wyatt, P. G.; Allen, M. J.; Borthwick, A. D. Bioorg. Med. Chem. Lett. 2005, 15, 2579.
  (b) Fischer, P. M. J. Pept. Sci. 2003, 9, 9.
  (c) O'Neill, J. C.; Blackwell, H. E. Comb. Chem. High Throughput Screening. 2007, 10, 857.
  (d) Merwe, E. V. D.; Huang, D.; Peterson, D.; Kilian, G.; Milne, P. J.; Venter, M. V. D. Peptides 2008, 29, 1305.
25. [25]
  Canu, N.; Belin, P.; Thai, R. Angew. Chem., Int. Ed. 2018, 57, 3118. doi: 10.1002/anie.201712536
26. [26]
  Moutiez, M.; Seguin, J.; Fonvielle, M.; Belin, P.; Jacques, I. B.; Favry, E.; Arthur, M.; Gondry, M. Nucleic Acids Res. 2014, 42, 7247. doi: 10.1093/nar/gku348
27. [27]
  Lautru, S.; Gondry, M.; Genet, R. Chem. Biol. 2002, 9, 1355. doi: 10.1016/S1074-5521(02)00285-5
28. [28]
  Moutiez, M.; Belin, P.; Gondry, M. Chem. Rev. 2017, 117, 5578. doi: 10.1021/acs.chemrev.6b00523
29. [29]
  Li, W. L.; Xia, J. Microb. China 2014, 41, 111 (in Chinese).
30. [30]
  Sauguet, L.; Moutiez, M.; Li, Y.; Belin, P.; Seguin, J.; Le Du, M.H.; Thai, R.; Masson, C.; Fonvielle, M.; Pernodet, J. L. Nucleic Acids Res. 2011, 39, 4475. doi: 10.1093/nar/gkr027
31. [31]
  Gondry, M.; Jacques, I. B.; Thai, R. Front. Microb. 2018, 9.
32. [32]
  Gondry, M.; Sauguet, L.; Belin, P. Nat. Chem. Biol. 2009, 5, 414. doi: 10.1038/nchembio.175
33. [33]
  Jacques, I. B.; Moutiez, M.; Witwinowski, J. Nat. Chem. Biol. 2015, 11, 721. doi: 10.1038/nchembio.1868
34. [34]
  (a) Brockmeyer, K.; Li, S. M. J. Nat. Prod. 2017, 80, 2917.
  (b) Mukai, T.; Reynolds, N. M.; Crnković, A. Life 2017, 7, 8.
  (c) Alqahtani, N.; Porwal, S. K.; James, E. D. Org. Biomol. Chem. 2015, 13, 7177.
  (d) Sievers, F.; Wilm, A.; Dineen, D.; Gibson, T.J.; Karplus, K.; Li, W.; Lopez, R.; McWilliam, H.; Remmert, M.; Soding, J. Mol. Syst. Biol. 2011, 7, 539.
35. [35]
  (a) Bonnefond, L.; Arai, T.; Sakaguchi, Y. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 3912.
  (b) Yaremchuk, A.; Kriklivyi, I.; Tukalo, M. EMBO J. 2002, 21, 3829.
  (c) Jacques, I.; Seguin, J.; Moutiez, M. New Biotechnol. 2014, 31, S74.
  (d) Cusack, S.; Berthet-Colominas, C.; Härtlein, M.; Nassar, N.; Leberman, R. Nature 1990, 347, 249.
36. [36]
37. [37]
  (a) Seguin, J.; Moutiez, M.; Li, Y. Chem. Biol. 2011, 18, 1362.
  (b) Minelli, A.; Bellezza, I.; Grottelli, S.; Galli, F. Amino Acids 2008, 35, 283.
  (c) Moutiez, M.; Schmitt, E.; Seguin, J. Nat. Commun. 2014, 5, 5141.
38. [38]
  Giessen, T. W.; von Tesmar, A. M.; Marahiel, M. A. Biochemistry 2013, 52, 4274. doi: 10.1021/bi4004827
39. [39]
  (a) Aravind, L.; De, S. R. F.; Iyer, L. M. Biol. Direct 2010, 5, 48.
  (b) Belin, P.; Moutiez, M.; Lautru, S. Nat. Prod. Rep. 2012, 29, 961.
  (c) Roback, P.; Beard, J.; Baumann, D. Nucleic Acids Res. 2007, 35, 5085.
40. [40]
  (a) Gondry, M.; Lautru, S.; Fusai, G. Eur. J. Biochem. 2001, 268, 1712.
  (b) Belin, P.; Le Du, M.H.; Fielding, A.; Lequin, O.; Jacquet, M.; Charbonnier, J. B.; Lecoq, A.; Thai, R.; Courcon, M.; Masson, C. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 7426.
  (c) Leys, D.; Mowat, C. G.; Mclean, K. J. J. Biol. Chem. 2003, 278, 5141.
  (d) Seward, H. E.; Roujeinikova, A.; Mclean, K. J. J. Biol. Chem. 2006, 281, 39437.
41. [41]
  (a) Bourgeois, G.; Seguin, J.; Babin, M. J. Struct. Biol. 2018.
  (b) Cryle, M. J.; Bell, S. G.; Schlichting, I. Biochemistry 2010, 49, 7282.
  (c) Tang, M. R.; Sternberg, D.; Behr, R. K. Ind. Biotechnol. 2006, 2, 66.
42. [42]
  Zhang, Q.; Li, S.; Chen, Y.; Tian, X.; Zhang, H.; Zhang, G.; Zhu, Y.; Zhang, S.; Zhang, W.; Zhang, C. J. Antibiot. 2013, 66, 31. doi: 10.1038/ja.2012.88
43. [43]
  Skinnider, M. A.; Johnston, C. W.; Merwin, N. J. BMC Genomics. 2018, 19, 45. doi: 10.1186/s12864-018-4435-1
44. [44]
  James, E. D.; Knuckley, B.; Alqahtani, N. ACS Synth. Biol. 2016, 5, 547. doi: 10.1021/acssynbio.5b00120
45. [45]
  Johnson, J. A.; Lu, Y. Y.; Van Devente, J. A. Curr. Opin. Chem. Biol. 2010, 14, 774. doi: 10.1016/j.cbpa.2010.09.013
46. [46]
  Giessen, T. W.; Altegoer, F.; Nebel, A. J.; Steinbach, R. M.; Bange, G.; Marahiel, M. A. Angew. Chem., Int. Ed. 2015, 54, 2492. doi: 10.1002/anie.201410047
47. [47]
  Giessen, T. W.; Marahiel, M. A. Front. Microb. 2015, 6, 785.
48. [48]
  McLean, K. J.; Cheesman, M.R.; Rivers, S.L.; Richmond, A.; Leys, D.; Chapman, S. K.; Reid, G. A.; Price, N. C.; Kelly, S. M.; Clarkson, J.; Smith, W. E.; Munro, A. W. J. Inorg. Biochem. 2002, 91, 527. doi: 10.1016/S0162-0134(02)00479-8
49. [49]
  Bonnefond, L.; Arai, T.; Sakaguchi, Y. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 3912. doi: 10.1073/pnas.1019480108
50. [50]
  Liu, J.; Yu, H.; Li, S. M. Appl. Microbiol. Biotechnol. 2018, 102, 4435. doi: 10.1007/s00253-018-8908-6
51. [51]
  Yao, T. T.; Liu, J.; Liu, Z. Z.; Li, T.; Li, H. Y.; Che, Q.; Zhu, T. J.; Li, D. H.; Gu, Q. Q.; Li, W. L. Nat. Commun. 2018, 9, 4091. doi: 10.1038/s41467-018-06411-x
52. [52]
  (a) Li, S. M. ChemInform 2010, 27, 57.
  (b) Xu, W.; Gavia, D. J.; Tang, Y. Nat. Prod. Rep. 2014, 31, 1474.
  (c) Alkhalaf, L. M.; Ryan, K. S. Chem. Biol. 2015, 22, 317.
  (d) Walsh, C. T. ACS Chem. Biol. 2014, 9, 2718.
53. [53]
  Fan, A.; Winkelblech, J.; Li, S. M. Appl. Microbiol. Biotechnol. 2015, 99, 7399. doi: 10.1007/s00253-015-6813-9
54. [54]
  (a) Meng, S.; Han, W.; Zhao, J.; Jian, X. H.; Pan, H. X.; Tang, G. L. Angew. Chem., Int. Ed. 2018, 57, 719.
  (b) Patteson, J.; Cai, W.; Johnson, R. A.; Santa, M. K.; Li, B. Biochemistry 2017, 57, 61.
55. [55]
  Kohn, H.; Widger, W. Curr. Drug Targets: Infect. Disord. 2005, 5, 273. doi: 10.2174/1568005054880136
56. [56]
  Schmitt, E.; Bourgeois, G.; Gondry, M.; Aleksandrov, A. Sci. Rep. 2018, 8, 7031. doi: 10.1038/s41598-018-25479-5
57. [57]
  Wunsch, C.; Mundt, K.; Li, S. M. Appl. Microbiol. Biotechnol. 2015, 99, 4213. doi: 10.1007/s00253-015-6490-8
58. [58]
  Vior, N. M.; Lacret, R.; Chandra, G.; Dorairaj, S.; Trick, M. & Truman, A. W. Appl. Environ. Microbiol. 2018, 84(9), UNSP/ e02828-17.
59. [59]
  Prasad, C. Peptides 1995, 16, 151. doi: 10.1016/0196-9781(94)00017-Z
60. [60]
  Giessen, T. W.; von Tesmar, A. M.; Marahiel, M. A. Chem. Biol. 2013, 20, 828. doi: 10.1016/j.chembiol.2013.04.017
1. [1]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
2. [2]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
3. [3]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
4. [4]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
5. [5]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
6. [6]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
7. [7]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
8. [8]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
9. [9]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
10. [10]
  Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
11. [11]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
12. [12]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
13. [13]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
14. [14]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
15. [15]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
16. [16]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
17. [17]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
18. [18]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
19. [19]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
20. [20]
  Zhuoya WANG , Le HE , Zhiquan LIN , Yingxi WANG , Ling LI . Multifunctional nanozyme Prussian blue modified copper peroxide: Synthesis and photothermal enhanced catalytic therapy of self-provided hydrogen peroxide. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2445-2454. doi: 10.11862/CJIC.20240194

Get Citation

PDF

XML

Metrics

PDF Downloads(101)
Abstract views(4451)
HTML views(1851)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142