Releasing the potential power of terpene synthases by a robust precursor supply platform

Metabolic Engineering

Volumn 42, Issue , 2017, Pages 1-8

  Bian, Guangkai ^a   Han, Yichao ^b   Hou, Anwei ^a   Yuan, Yujie ^a   Liu, Xinhua ^a   Deng, Zixin ^a,c   Liu, Tiangang ^a,c  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

^b Wuhan J1 Biotech Co Ltd   (China)

^c Wuhan Institute of Biotechnology   (China)

Author keywords

Combinatorial biosynthesis; Precursor supply; Promiscuous; Protein engineering; Skeleton reframing; Terpene synthases; Terpenoids

Indexed keywords

BIOCHEMISTRY; BIOSYNTHESIS; LIPIDS; METABOLIC ENGINEERING; MUSCULOSKELETAL SYSTEM;

COMBINATORIAL BIOSYNTHESIS; PRECURSOR SUPPLY; PROMISCUOUS; PROTEIN ENGINEERING; REFRAMING; SYNTHASES; TERPENOIDS;

TERPENES;

BACTERIAL PROTEIN; ISOPRENOID PHOSPHATE; TERPENE SYNTHASE; TRANSFERASE;

CHEMISTRY; GENETICS; POINT MUTATION;

ALKYL AND ARYL TRANSFERASES; BACTERIAL PROTEINS; POINT MUTATION; POLYISOPRENYL PHOSPHATES;

EID: 85019157109     PISSN: 10967176     EISSN: 10967184     Source Type: Journal    
DOI: 10.1016/j.ymben.2017.04.006     Document Type: Article

References (40)

1. Agger, S.A., Lopez-Gallego, F., Hoye, T.R., Schmidt-Dannert, C., Identification of sesquiterpene synthases from Nostoc punctiforme PCC 73102 and Nostoc sp. strain PCC 7120. J. Bacteriol. 190 (2008), 6084–6096.
2. Aharoni, A., Giri, A.P., Verstappen, F.W., Bertea, C.M., Sevenier, R., Sun, Z., Jongsma, M.A., Schwab, W., Bouwmeester, H.J., Gain and loss of fruit flavor compounds produced by wild and cultivated strawberry species. Plant Cell. 16 (2004), 3110–3131.
3. Ajikumar, P.K., Xiao, W.-H., Tyo, K.E.J., Wang, Y., Simeon, F., Leonard, E., Mucha, O., Phon, T.H., Pfeifer, B., Stephanopoulos, G., Isoprenoid pathway optimization for Taxol precursor overproduction in Escherichia coli. Science 330 (2010), 70–74.
4. Andersen-Ranberg, J., Kongstad, K.T., Nielsen, M.T., Jensen, N.B., Pateraki, I., Bach, S.S., Hamberger, B., Zerbe, P., Staerk, D., Bohlmann, J., Moller, B.L., Hamberger, B., Expanding the landscape of diterpene structural diversity through stereochemically controlled combinatorial biosynthesis. Angew. Chem. 55 (2016), 2142–2146.
5. Biggs, B.W., Lim, C.G., Sagliani, K., Shankar, S., Stephanopoulos, G., De Mey, M., Ajikumar, P.K., Overcoming heterologous protein interdependency to optimize P450-mediated Taxol precursor synthesis in Escherichia coli. Proc. Natl. Acad. Sci. Usa. 113 (2016), 3209–3214.
6. Cane, D.E., Walsh, C.T., Khosla, C., Harnessing the biosynthetic code: combinations, permutations, and mutations. Science 282 (1998), 63–68.
7. Chen, M., Chou, W.K.W., Toyomasu, T., Cane, D.E., Christianson, D.W., Structure and function of fusicoccadiene synthase, a hexameric bifunctional diterpene synthase. ACS Chem. Biol. 11 (2016), 889–899.
8. Chiba, R., Minami, A., Gomi, K., Oikawa, H., Identification of ophiobolin F synthase by a genome mining approach: a sesterterpene synthase from Aspergillus clavatus. Org. Lett. 15 (2013), 594–597.
9. Christianson, D.W., Structural biology and chemistry of the terpenoid cyclases. Chem. Rev. 106 (2006), 3412–3442.
10. Dickschat, J.S., Bacterial terpene cyclases. Nat. Prod. Rep. 33 (2016), 87–110.
11. Fischbach, M.A., Clardy, J., One pathway, many products. Nat. Chem. Biol. 3 (2007), 353–355.
12. Fujimoto, H., Nakamura, E., Okuyama, E., Ishibashi, M., Immunomodulatory constituents from an ascomycete, Emericella aurantio-brunnea. Chem. Pharm. Bull. 48 (2000), 1436–1441.
13. Furubayashi, M., Ikezumi, M., Takaichi, S., Maoka, T., Hemmi, H., Ogawa, T., Saito, K., Tobias, A.V., Umeno, D., A highly selective biosynthetic pathway to non-natural C50 carotenoids assembled from moderately selective enzymes. Nat. Commun., 6, 2015, 7534.
14. Hensens, O.D., Zink, D., Williamson, J.M., Lotti, V.J., Chang, R.S.L., Goetz, M.A., Variecolin, a sesterterpenoid of novel skeleton from Aspergillus variecolor MF138. J. Org. Chem. 56 (1991), 3399–3403.
15. Jia, M., Potter, K.C., Peters, R.J., Extreme promiscuity of a bacterial and a plant diterpene synthase enables combinatorial biosynthesis. Metab. Eng. 37 (2016), 24–34.
16. Katoh, K., Misawa, K., Kuma, K. i., Miyata, T., MAFFT: a novel method for rapid multiple sequence alignment based on fast Fourier transform. Nucleic Acids Res. 30 (2002), 3059–3066.
17. Kellogg, B.A., Poulter, C.D., Chain elongation in the isoprenoid biosynthetic pathway. Curr. Opin. Chem. Biol. 1 (1997), 570–578.
18. Khosla, C., Herschlag, D., Cane, D.E., Walsh, C.T., Assembly line polyketide synthases: mechanistic insights and unsolved problems. Biochemistry 53 (2014), 2875–2883.
19. Kim, E., Moore, B.S., Yoon, Y.J., Reinvigorating natural product combinatorial biosynthesis with synthetic biology. Nat. Chem. Biol. 11 (2015), 649–659.
20. Kumar, S., Stecher, G., Tamura, K., MEGA7: molecular evolutionary genetics analysis version 7.0 for bigger datasets. Mol. Biol. Evol., 2016 (msw054).
21. Leavell, M.D., McPhee, D.J., Paddon, C.J., Developing fermentative terpenoid production for commercial usage. Curr. Opin. Biotechnol. 37 (2016), 114–119.
22. Li, R., Chou, W.K.W., Himmelberger, J.A., Litwin, K.M., Harris, G.G., Cane, D.E., Christianson, D.W., Reprogramming the chemodiversity of terpenoid cyclization by remolding the active site contour of epi-isozizaene synthase. Biochemistry 53 (2014), 1155–1168.
23. Ma, T., Zhou, Y., Li, X., Zhu, F., Cheng, Y., Liu, Y., Deng, Z., Liu, T., Genome mining of astaxanthin biosynthetic genes from Sphingomonas sp. ATCC 55669 for heterologous overproduction in Escherichia coli. Biotechnol. J. 11 (2016), 228–237.
24. Mafu, S., Jia, M., Zi, J., Morrone, D., Wu, Y., Xu, M., Hillwig, M.L., Peters, R.J., Probing the promiscuity of ent-kaurene oxidases via combinatorial biosynthesis. Proc. Natl. Acad. Sci. Usa. 113 (2016), 2526–2531.
25. Maimone, T.J., Baran, P.S., Modern synthetic efforts toward biologically active terpenes. Nat. Chem. Biol. 3 (2007), 396–407.
26. Meguro, A., Tomita, T., Nishiyama, M., Kuzuyama, T., Identification and characterization of bacterial diterpene cyclases that synthesize the cembrane skeleton. ChemBioChem 14 (2013), 316–321.
27. Nagegowda, D.A., Gutensohn, M., Wilkerson, C.G., Dudareva, N., Two nearly identical terpene synthases catalyze the formation of nerolidol and linalool in snapdragon flowers. Plant J. 55 (2008), 224–239.
28. Qin, B., Matsuda, Y., Mori, T., Okada, M., Quan, Z., Mitsuhashi, T., Wakimoto, T., Abe, I., An unusual chimeric diterpene synthase from Emericella variecolor and its functional conversion into a sesterterpene synthase by domain swapping. Angew. Chem. Int. Ed. 55 (2016), 1658–1661.
29. Renner, M.K., Jensen, P.R., Fenical, W., Mangicols: structures and biosynthesis of a new class of sesterterpene polyols from a marine fungus of the genus Fusarium. J. Org. Chem. 65 (2000), 4843–4852.
30. Sieber, S.A., Marahiel, M.A., Molecular mechanisms underlying nonribosomal peptide synthesis: approaches to new antibiotics. Chem. Rev. 105 (2005), 715–738.
31. Stockdale, T.P., Williams, C.M., Pharmaceuticals that contain polycyclic hydrocarbon scaffolds. Chem. Soc. Rev. 44 (2015), 7737–7763.
32. Tian, B., Poulter, C.D., Jacobson, M.P., Defining the product chemical space of monoterpenoid synthases. PLoS Comput. Biol., 12, 2016, e1005053.
33. Tsoi, C.J., Khosla, C., Combinatorial biosynthesis of ‘unnatural'natural products: the polyketide example. Chem. Biol. 2 (1995), 355–362.
34. Wang, C., Park, J.E., Choi, E.S., Kim, S.W., Farnesol production in Escherichia coli through the construction of a farnesol biosynthesis pathway–application of PgpB and YbjG phosphatases. Biotechnol. J. 11 (2016), 1291–1297.
35. Weissman, K.J., Leadlay, P.F., Combinatorial biosynthesis of reduced polyketides. Nat. Rev. Microbiol. 3 (2005), 925–936.
36. Xiao, Z. e., Huang, H., Shao, C., Xia, X., Ma, L., Huang, X., Lu, Y., Lin, Y., Long, Y., She, Z., Asperterpenols A and B, new sesterterpenoids isolated from a mangrove endophytic fungus Aspergillus sp. 085242. Org. Lett. 15 (2013), 2522–2525.
37. Yamada, Y., Kuzuyama, T., Komatsu, M., Shin-ya, K., Omura, S., Cane, D.E., Ikeda, H., Terpene synthases are widely distributed in bacteria. Proc. Natl. Acad. Sci. Usa. 112 (2015), 857–862.
38. Ye, Y., Minami, A., Mandi, A., Liu, C., Taniguchi, T., Kuzuyama, T., Monde, K., Gomi, K., Oikawa, H., Genome mining for sesterterpenes using bifunctional terpene synthases reveals a unified intermediate of di/sesterterpenes. J. Am. Chem. Soc. 137 (2015), 11846–11853.
39. Zhu, F., Zhong, X., Hu, M., Lu, L., Deng, Z., Liu, T., In vitro reconstitution of mevalonate pathway and targeted engineering of farnesene overproduction in Escherichia coli. Biotechnol. Bioeng. 111 (2014), 1396–1405.
40. Zhu, F., Lu, L., Fu, S., Zhong, X., Hu, M., Deng, Z., Liu, T., Targeted engineering and scale up of lycopene overproduction in Escherichia coli. Process Biochem. 50 (2015), 341–346.