Production of δ-decalactone from linoleic acid via 13-hydroxy-9(Z)-octadecenoic acid intermediate by one-pot reaction using linoleate 13-hydratase and whole Yarrowia lipolytica cells

Kang, Woo-Ri; Seo, Min‐Ju; An, Jung-Ung; Shin, Kyung‐Chul; Oh, Deok‐Kun

doi:10.1007/s10529-016-2041-3

Cited by 15 publications

(8 citation statements)

References 11 publications

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“…This accords with the contribution of FAO1 to diacid production observed in C. tropicalis [95]. Various fatty aldehyde dehydrogenases have been identified in Y. lipolytica that are involved in the detoxification of fatty acid aldehyde intermediates by oxidizing them to dicarboxylic acids [96][97][98]. These native genes likely contribute to the background ω-oxidation activity.…”

Section: Discussionsupporting

confidence: 77%

Combinatorial Engineering of Yarrowia lipolytica as a Promising Cell Biorefinery Platform for the de novo Production of Multi-Purpose Long Chain Dicarboxylic Acids

2017

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This proof-of-concept study establishes Yarrowia lipolytica (Y. lipolytica) as a whole cell factory for the de novo production of long chain dicarboxylic acid (LCDCA-16 and 18) using glycerol as the sole source of carbon. Modification of the fatty acid metabolism pathway enabled creating a pool of fatty acids in a β-oxidation deficient strain. We then selectively upregulated the native fatty acid ω-oxidation pathway for the enhanced terminal oxidation of the endogenous fatty acid precursors. Nitrogen-limiting conditions and leucine supplementation were employed to induce fatty acid biosynthesis in an engineered Leu -modified strain. Our genetic engineering strategy allowed a minimum production of 330 mg/L LCDCAs in shake flask. Scale up to a 1-L bioreactor increased the titer to 3.49 g/L. Our engineered yeast also produced citric acid as a major by-product at a titer of 39.2 g/L. These results provide basis for developing Y. lipolytica as a safe biorefinery platform for the sustainable production of high-value LCDCAs from non-oily feedstock.

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Section: Discussionsupporting

confidence: 77%

Combinatorial Engineering of Yarrowia lipolytica as a Promising Cell Biorefinery Platform for the de novo Production of Multi-Purpose Long Chain Dicarboxylic Acids

2017

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“…The hydration reaction of unsaturated fatty acids was discovered in the early 1960s, during a study on the hydration of oleic acid using a Pseudomonas strain [9,10]. Afterwards, a number of other microorganisms proved to be able to perform this transformation [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] but the enzymes responsible for the hydration step (oleate hydratases) have been characterized only recently [26], receiving growing attention both from chemists and biologists [27][28][29][30][31][32][33][34][35][36][37]. It is worth noting that different putative oleate hydratase have been cloned from a number of bacteria strains, but none of them have been used for the industrial synthesis of HFAs.…”

Section: Introductionmentioning

confidence: 99%

Use of Lactobacillus rhamnosus (ATCC 53103) as Whole-Cell Biocatalyst for the Regio- and Stereoselective Hydration of Oleic, Linoleic, and Linolenic Acid

Serra

Simeis

2018

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Natural hydroxy fatty acids are relevant starting materials for the production of a number of industrial fine chemicals, such as different high-value flavour ingredients. Only a few of the latter hydroxy acid derivatives are available on a large scale. Therefore, their preparation by microbial hydration of unsaturated fatty acids, affordable from vegetable oils, is a new biotechnological challenge. In this study, we describe the use of the probiotic bacterium Lactobacillus rhamnosus (ATCC 53103) as whole-cell biocatalyst for the hydration of the most common unsaturated octadecanoic acids, namely oleic acid, linoleic acid, and linolenic acid. We discovered that the addition of the latter fatty acids to an anaerobic colture of the latter strain, during the early stage of its exponential growth, allows the production of the corresponding mono-hydroxy derivatives. In these experimental conditions, the hydration reaction proceeds with high regio-and stereoselectivity. Only 10-hydroxy derivatives were formed and the resulting (R)-10-hydroxystearic acid, (S)-(12Z)-10-hydroxy-octadecenoic acid, and (S)-(12Z,15Z)-10-hydroxy-octadecadienoic acid were obtained in very high enantiomeric purity (ee > 95%). Although overall conversions usually do not exceed 50% yield, our biotransformation protocol is stereoselective, scalable, and holds preparative significance.

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“…Fatty acid hydratases (FAHYs;E C4.2.1.X) catalyze the formation of medium-and long-chain hydroxylated fatty acids by addition of water to isolated carbon-carbon double bonds of free mono-or polyunsaturated fatty acids. [1][2][3][4][5] As such, they provide access to secondary and tertiary alcohols, which makes them valuable tools for the production of av ariety of chemicals,i ncluding flavor additives, [6][7][8] surfactants,lubricants,and precursors in polymer chemistry. [9][10][11][12][13] The use of FAHYs in synthesis promises advantages relating to their exquisite regio-and stereoselectivity,w hich permits reactions that are not possible with unselective acid-catalyzed chemical hydrations.…”

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confidence: 99%

Evolving the Promiscuity of Elizabethkingia meningoseptica Oleate Hydratase for the Regio‐ and Stereoselective Hydration of Oleic Acid Derivatives

et al. 2019

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The addition of water to non‐activated carbon–carbon double bonds catalyzed by fatty acid hydratases (FAHYs) allows for highly regio‐ and stereoselective oxyfunctionalization of renewable oil feedstock. So far, the applicability of FAHYs has been limited to free fatty acids, mainly owing to the requirement of a carboxylate function for substrate recognition and binding. Herein, we describe for the first time the hydration of oleic acid (OA) derivatives lacking this free carboxylate by the oleate hydratase from Elizabethkingia meningoseptica (OhyA). Molecular docking of OA to the OhyA 3D‐structure and a sequence alignment uncovered conserved amino acid residues at the entrance of the substrate channel as target positions for enzyme engineering. Exchange of selected amino acids gave rise to OhyA variants which showed up to an 18‐fold improved conversion of OA derivatives, while retaining the excellent regio‐ and stereoselectivity in the olefin hydration reaction.

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Production of δ-decalactone from linoleic acid via 13-hydroxy-9(Z)-octadecenoic acid intermediate by one-pot reaction using linoleate 13-hydratase and whole Yarrowia lipolytica cells

Abstract: To the best of our knowledge, this is the first production of δ-decalactone using unsaturated fatty acid.

Cited by 15 publications

References 11 publications

Combinatorial Engineering of Yarrowia lipolytica as a Promising Cell Biorefinery Platform for the de novo Production of Multi-Purpose Long Chain Dicarboxylic Acids

Combinatorial Engineering of Yarrowia lipolytica as a Promising Cell Biorefinery Platform for the de novo Production of Multi-Purpose Long Chain Dicarboxylic Acids

Use of Lactobacillus rhamnosus (ATCC 53103) as Whole-Cell Biocatalyst for the Regio- and Stereoselective Hydration of Oleic, Linoleic, and Linolenic Acid

Evolving the Promiscuity of Elizabethkingia meningoseptica Oleate Hydratase for the Regio‐ and Stereoselective Hydration of Oleic Acid Derivatives

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