Synthesis of rosmarinic acid analogues in Escherichia coli

Yibin Zhuang; Jingjie Jiang; Huiping Bi; Hua Yin; Shaowei Liu; Tao Liu

doi:10.1007/s10529-015-2011-1

Synthesis of rosmarinic acid analogues in Escherichia coli

Biotechnol Lett. 2016 Apr;38(4):619-27. doi: 10.1007/s10529-015-2011-1. Epub 2015 Dec 14.

Authors

Yibin Zhuang^{1

2}, Jingjie Jiang^{1

3}, Huiping Bi^{1

2}, Hua Yin^{1

2}, Shaowei Liu⁴, Tao Liu^{5

6}

Affiliations

¹ Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin, 300308, China.
² Key Laboratory of Systems Microbial Biotechnology, Chinese Academy of Sciences, Tianjin, 300308, China.
³ Department of Food Science and Technology, School of Biological Engineering, East China University of Science and Technology, Shanghai, 200237, China.
⁴ Department of Food Science and Technology, School of Biological Engineering, East China University of Science and Technology, Shanghai, 200237, China. swliu@ecust.edu.cn.
⁵ Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin, 300308, China. liu_t@tib.cas.cn.
⁶ Key Laboratory of Systems Microbial Biotechnology, Chinese Academy of Sciences, Tianjin, 300308, China. liu_t@tib.cas.cn.

PMID: 26667131
DOI: 10.1007/s10529-015-2011-1

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.

Keywords: 4-Coumarate:CoA ligase; Biosynthesis; Escherichia coli; Phenyllactic acid; Rosmarinic acid analogues; Rosmarinic acid synthase.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cinnamates / metabolism*
Coenzyme A Ligases / genetics
Coenzyme A Ligases / metabolism
Depsides
Escherichia coli / enzymology
Escherichia coli / genetics
Escherichia coli / growth & development*
Escherichia coli Proteins / genetics
Escherichia coli Proteins / metabolism
Metabolic Engineering / methods
Rosmarinic Acid
Substrate Specificity

Substances

Cinnamates
Depsides
Escherichia coli Proteins
Coenzyme A Ligases