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

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

doi:10.1186/s12934-016-0593-5

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

Journal Article · Mon Nov 21 00:00:00 EST 2016 · Microbial Cell Factories

DOI:https://doi.org/10.1186/s12934-016-0593-5· OSTI ID:1393089

Eudes, Aymerick ^[1]; Mouille, Maxence ^[1]; Robinson, David S. ^[2]; Benites, Veronica T. ^[3]; Wang, George ^[1]; Roux, Lucien ^[4]; Tsai, Yi-Lin ^[1]; Baidoo, Edward E. K. ^[1]; Chiu, Tsan-Yu ^[1]; Heazlewood, Joshua L. ^[5]; Scheller, Henrik V. ^[1]; Mukhopadhyay, Aindrila ^[1]; Keasling, Jay D. ^[6]; Deutsch, Samuel ^[2];

^[7]

Joint BioEnergy Institute, Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Joint BioEnergy Institute, Emeryville, CA (United States)
Joint BioEnergy Institute, Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); San Francisco State Univ., San Francisco, CA (United States)
Joint BioEnergy Institute, Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Ecole Polytechnique Federale de Lausanne, Lausanne (Switzerland)
Joint BioEnergy Institute, Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); The Univ. of Melbourne, Melbourne, VIC (Australia)
Joint BioEnergy Institute, Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of California, Berkeley, CA (United States); Technical Univ. of Denmark, Horsholm (Denmark)
Joint BioEnergy Institute, Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. Claude Bernard Lyon 1, Villeurbanne (France)

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.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

DOE Contract Number:: AC02-05CH11231

OSTI ID:: 1393089

Journal Information:: Microbial Cell Factories, Vol. 15, Issue 1; ISSN 1475-2859

Publisher:: BioMed Central

Country of Publication:: United States

Language:: English

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Related Subjects

59 BASIC BIOLOGICAL SCIENCES
Yeast
BAHD
Antioxidant
Therapeutics
Flavors and fragrances
CAPE

Exploiting members of the BAHD acyltransferase family to synthesize multiple hydroxycinnamate and benzoate conjugates in yeast Eudes, Aymerick; Mouille, Maxence; Robinson, David https://doi.org/10.6084/m9.figshare.c.3625478 The current record is supplemented by this dataset	dataset	November 2016
Exploiting members of the BAHD acyltransferase family to synthesize multiple hydroxycinnamate and benzoate conjugates in yeast [Supplemental Data] Eudes, Aymerick; Mouille, Maxence; Robinson, David https://doi.org/10.6084/m9.figshare.c.3625478.v1 The current record is supplemented by this dataset	dataset	November 2016
MOESM1 of Exploiting members of the BAHD acyltransferase family to synthesize multiple hydroxycinnamate and benzoate conjugates in yeast Eudes, Aymerick; Mouille, Maxence; Robinson, David https://doi.org/10.6084/m9.figshare.c.3625478_d1.v1 The current record is supplemented by this figure	figure	November 2016
MOESM1 of Exploiting members of the BAHD acyltransferase family to synthesize multiple hydroxycinnamate and benzoate conjugates in yeast Eudes, Aymerick; Mouille, Maxence; Robinson, David https://doi.org/10.6084/m9.figshare.c.3625478_d1 The current record is supplemented by this text	text	January 2016