Abstract
Objectives
To produce rosmarinic acid analogues in the recombinant Escherichia coli BLRA1, harboring a 4-coumarate: CoA ligase from Arabidopsis thaliana (At4CL) and a rosmarinic acid synthase from Coleus blumei (CbRAS).
Results
Incubation of the recombinant E. coli strain BLRA1 with exogenously supplied phenyllactic acid (PL) and analogues as acceptor substrates, and coumaric acid and analogues as donor substrates led to production of 18 compounds, including 13 unnatural RA analogues.
Conclusion
This work demonstrates the viability of synthesizing a broad range of rosmarinic acid analogues in E. coli, and sheds new light on the substrate specificity of CbRAS.
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Acknowledgments
This work was supported by grants from the 973 Program of China (no. 2012CB721100), the 863 Program of China (no. 2012AA02A704), the 100 Talents Program of the Chinese Academy of Sciences and the National Natural Science Foundation of China (nos. 21302214, 31300040, and 31400026).
Supporting information
Supplementary NMR data for compounds 3–15.
Supplementary Fig. 1—HPLC–MS analysis of metabolite profile of the recombinant E. coli strain BLRA1 supplied with ferulic acid and other substrates.
Supplementary Fig. 2—HPLC–MS analysis of metabolite profile of the recombinant E. coli strain BLRA1 supplied with p-hydroxyphenyl propionic acid (HPPA) and other substrates.
Supplementary Fig. 3—HPLC–MS analysis of metabolites profile of recombinant E. coli strain BLRA1 supplied with mandelic acid and other substrates.
Supplementary Fig. 4—HPLC–MS analysis of fermentation broth of recombinant E. coli strain BLRA1 fed with tyrosol and other substrates.
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Yibin Zhuang, Jingjie Jiang, and Huiping Bi have contributed equally to this article.
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Zhuang, Y., Jiang, J., Bi, H. et al. Synthesis of rosmarinic acid analogues in Escherichia coli . Biotechnol Lett 38, 619–627 (2016). https://doi.org/10.1007/s10529-015-2011-1
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DOI: https://doi.org/10.1007/s10529-015-2011-1