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Title: Exploiting members of the BAHD acyltransferase family to synthesize multiple hydroxycinnamate and benzoate conjugates in yeast

Abstract

BAHD acyltransferases, named after the first four biochemically characterized enzymes of the group, are plant-specific enzymes that catalyze the transfer of coenzyme A-activated donors onto various acceptor molecules. They are responsible for the synthesis in plants of a myriad of secondary metabolites, some of which are beneficial for humans either as therapeutics or as specialty chemicals such as flavors and fragrances. The production of pharmaceutical, nutraceutical and commodity chemicals using engineered microbes is an alternative, green route to energy-intensive chemical syntheses that consume petroleum-based precursors. However, identification of appropriate enzymes and validation of their functional expression in heterologous hosts is a prerequisite for the design and implementation of metabolic pathways in microbes for the synthesis of such target chemicals. As a result, for the synthesis of valuable metabolites in the yeast Saccharomyces cerevisiae, we selected BAHD acyltransferases based on their preferred donor and acceptor substrates. In particular, BAHDs that use hydroxycinnamoyl-CoAs and/or benzoyl-CoA as donors were targeted because a large number of molecules beneficial to humans belong to this family of hydroxycinnamate and benzoate conjugates. The selected BAHD coding sequences were synthesized and cloned individually on a vector containing the Arabidopsis gene At4CL5, which encodes a promiscuous 4-coumarate:CoA ligase activemore » on hydroxycinnamates and benzoates. The various S. cerevisiae strains obtained for co-expression of At4CL5 with the different BAHDs effectively produced a wide array of valuable hydroxycinnamate and benzoate conjugates upon addition of adequate combinations of donors and acceptor molecules. In particular, we report here for the first time the production in yeast of rosmarinic acid and its derivatives, quinate hydroxycinnamate esters such as chlorogenic acid, and glycerol hydroxycinnamate esters. Similarly, we achieved for the first time the microbial production of polyamine hydroxycinnamate amides; monolignol, malate and fatty alcohol hydroxycinnamate esters; tropane alkaloids; and benzoate/caffeate alcohol esters. In some instances, the additional expression of Flavobacterium johnsoniae tyrosine ammonia-lyase (FjTAL) allowed the synthesis of p-coumarate conjugates and eliminated the need to supplement the culture media with 4-hydroxycinnamate. In conclusion, we demonstrate in this study the effectiveness of expressing members of the plant BAHD acyltransferase family in yeast for the synthesis of numerous valuable hydroxycinnamate and benzoate conjugates.« less

Authors:
; ; ; ; ; ; ; ; ; ; ; ; ; ; ORCiD logo
Publication Date:
Research Org.:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1618805
Alternate Identifier(s):
OSTI ID: 1379589
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Published Article
Journal Name:
Microbial Cell Factories
Additional Journal Information:
Journal Name: Microbial Cell Factories Journal Volume: 15 Journal Issue: 1; Journal ID: ISSN 1475-2859
Publisher:
Springer Science + Business Media
Country of Publication:
United Kingdom
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; Yeast; BAHD; Antioxidant; Therapeutics; Flavors and fragrances; CAPE

Citation Formats

Eudes, Aymerick, Mouille, Maxence, Robinson, David S., Benites, Veronica T., Wang, George, Roux, Lucien, Tsai, Yi-Lin, Baidoo, Edward E. K., Chiu, Tsan-Yu, Heazlewood, Joshua L., Scheller, Henrik V., Mukhopadhyay, Aindrila, Keasling, Jay D., Deutsch, Samuel, and Loqué, Dominique. Exploiting members of the BAHD acyltransferase family to synthesize multiple hydroxycinnamate and benzoate conjugates in yeast. United Kingdom: N. p., 2016. Web. doi:10.1186/s12934-016-0593-5.
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Eudes, Aymerick, Mouille, Maxence, Robinson, David S., Benites, Veronica T., Wang, George, Roux, Lucien, Tsai, Yi-Lin, Baidoo, Edward E. K., Chiu, Tsan-Yu, Heazlewood, Joshua L., Scheller, Henrik V., Mukhopadhyay, Aindrila, Keasling, Jay D., Deutsch, Samuel, & Loqué, Dominique. Exploiting members of the BAHD acyltransferase family to synthesize multiple hydroxycinnamate and benzoate conjugates in yeast. United Kingdom. https://doi.org/10.1186/s12934-016-0593-5
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Eudes, Aymerick, Mouille, Maxence, Robinson, David S., Benites, Veronica T., Wang, George, Roux, Lucien, Tsai, Yi-Lin, Baidoo, Edward E. K., Chiu, Tsan-Yu, Heazlewood, Joshua L., Scheller, Henrik V., Mukhopadhyay, Aindrila, Keasling, Jay D., Deutsch, Samuel, and Loqué, Dominique. Mon . "Exploiting members of the BAHD acyltransferase family to synthesize multiple hydroxycinnamate and benzoate conjugates in yeast". United Kingdom. https://doi.org/10.1186/s12934-016-0593-5.
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@article{osti_1618805,
title = {Exploiting members of the BAHD acyltransferase family to synthesize multiple hydroxycinnamate and benzoate conjugates in yeast},
author = {Eudes, Aymerick and Mouille, Maxence and Robinson, David S. and Benites, Veronica T. and Wang, George and Roux, Lucien and Tsai, Yi-Lin and Baidoo, Edward E. K. and Chiu, Tsan-Yu and Heazlewood, Joshua L. and Scheller, Henrik V. and Mukhopadhyay, Aindrila and Keasling, Jay D. and Deutsch, Samuel and Loqué, Dominique},
abstractNote = {BAHD acyltransferases, named after the first four biochemically characterized enzymes of the group, are plant-specific enzymes that catalyze the transfer of coenzyme A-activated donors onto various acceptor molecules. They are responsible for the synthesis in plants of a myriad of secondary metabolites, some of which are beneficial for humans either as therapeutics or as specialty chemicals such as flavors and fragrances. The production of pharmaceutical, nutraceutical and commodity chemicals using engineered microbes is an alternative, green route to energy-intensive chemical syntheses that consume petroleum-based precursors. However, identification of appropriate enzymes and validation of their functional expression in heterologous hosts is a prerequisite for the design and implementation of metabolic pathways in microbes for the synthesis of such target chemicals. As a result, for the synthesis of valuable metabolites in the yeast Saccharomyces cerevisiae, we selected BAHD acyltransferases based on their preferred donor and acceptor substrates. In particular, BAHDs that use hydroxycinnamoyl-CoAs and/or benzoyl-CoA as donors were targeted because a large number of molecules beneficial to humans belong to this family of hydroxycinnamate and benzoate conjugates. The selected BAHD coding sequences were synthesized and cloned individually on a vector containing the Arabidopsis gene At4CL5, which encodes a promiscuous 4-coumarate:CoA ligase active on hydroxycinnamates and benzoates. The various S. cerevisiae strains obtained for co-expression of At4CL5 with the different BAHDs effectively produced a wide array of valuable hydroxycinnamate and benzoate conjugates upon addition of adequate combinations of donors and acceptor molecules. In particular, we report here for the first time the production in yeast of rosmarinic acid and its derivatives, quinate hydroxycinnamate esters such as chlorogenic acid, and glycerol hydroxycinnamate esters. Similarly, we achieved for the first time the microbial production of polyamine hydroxycinnamate amides; monolignol, malate and fatty alcohol hydroxycinnamate esters; tropane alkaloids; and benzoate/caffeate alcohol esters. In some instances, the additional expression of Flavobacterium johnsoniae tyrosine ammonia-lyase (FjTAL) allowed the synthesis of p-coumarate conjugates and eliminated the need to supplement the culture media with 4-hydroxycinnamate. In conclusion, we demonstrate in this study the effectiveness of expressing members of the plant BAHD acyltransferase family in yeast for the synthesis of numerous valuable hydroxycinnamate and benzoate conjugates.},
doi = {10.1186/s12934-016-0593-5},
journal = {Microbial Cell Factories},
number = 1,
volume = 15,
place = {United Kingdom},
year = {Mon Nov 21 00:00:00 EST 2016},
month = {Mon Nov 21 00:00:00 EST 2016}
}
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https://doi.org/10.1186/s12934-016-0593-5
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Cited by: 25 works
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Figures / Tables:

Fig. 1 Fig. 1: Mechanism of acylation catalyzed by BAHD acyltransferases. Acyl donors are activated upon esterification of their carboxylic group (COOH) with coenzyme A (CoA). BAHD acyltransferases using 4-hydroxycinnamoyl-CoAs (R = 4-hydroxystyrene) and benzoyl-CoAs (R = benzene) as donors were used for this study. R’ = BAHD acceptor
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