Production of 13S-hydroxy-9(Z)-octadecenoic acid from linoleic acid by whole recombinant cells expressing linoleate 13-hydratase from Lactobacillus acidophilus

Park, Jiyoung; Lee, Seon Hwa; Kim, Kyoung-Rok; Park, Jin Byung; Oh, Deok‐Kun

doi:10.1016/j.jbiotec.2015.05.006

Cited by 31 publications

(13 citation statements)

References 39 publications

(47 reference statements)

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“…In contrast, linoleic acid was transformed into a mixture of (12Z)-10-hydroxy-octadecenoic acid (6), (9Z)-13-hydroxyoctadecenoic acid (8), and 10,13-dihydroxy-octadecenoic acid (9a) in high overall yield. Both absolute configuration and enantiomeric purity of compounds 6 and 8 were determined by NMR analysis of their corresponding (S)-O-acetylmandelate derivatives of the methyl esters, according to previously reported studies [12,39]. These means confirmed that the investigated microorganism holds hydratase activity similar to that reported for other Lactobacillus acidophilus strains, affording (S)-(12Z)-10-hydroxy-octadecenoic acid (6) and (S)-(9Z)-13-hydroxy-octadecenoic acid (8) in high enantiomeric purity.…”

Section: Resultsmentioning

confidence: 99%

“…Concerning (9Z)-13-hydroxy-octadecenoic acid samples, their absolute configuration was assigned by comparing the 1 H-NMR analysis of the corresponding (S)-O-acetylmandelates with that reported for the same derivative obtained, starting from (S)-(9Z)-13-hydroxy-octadecenoic acid [39].…”

Section: Determination Of the Absolute Configuration And Of The Opticmentioning

confidence: 99%

“…Nevertheless, only few relevant exceptions to this general trend have been reported. An important example concerns some strains of Lactobacillus acidophilus [39][40][41] and Lactobacillus plantarum [42] that As stated previously, HFAs are usually formed with high regio-and stereoselectivity. According to our recent work [12], the widely used probiotic Lactobacillus rhamnosus LGG converts acids 1-3 into the corresponding 10-hydroxy derivatives, namely (R)-10-hydroxystearic acid (4), (S)-(12Z)-10-hydroxy-octadecenoic acid (6), and (S)-(12Z,15Z)-10-hydroxy-octadecadienoic acid (10), respectively, in very high enantiomeric purity (ee > 95%).…”

Section: Introductionmentioning

confidence: 99%

“…Nevertheless, only few relevant exceptions to this general trend have been reported. An important example concerns some strains of Lactobacillus acidophilus [39][40][41] and Lactobacillus plantarum [42] that possess both 10and 13-hydratase activity, most likely due to the simultaneous activity of two different enzymes. Therefore, the whole-cell biotransformation of linolenic acid using the latter microorganisms can afford a mixture of (S)-(12Z)-10-hydroxy-octadecenoic acid (6), (S)-(9Z)-13-hydroxy-octadecenoic acid (8), and (10S,13S)-10,13-dihydroxy-octadecenoic acid (9).…”

Section: Introductionmentioning

confidence: 99%

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The Fatty-Acid Hydratase Activity of the Most Common Probiotic Microorganisms

Serra¹,

Simeis²,

Castagna³

et al. 2020

Catalysts

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In this work, we studied the biotechnological potential of thirteen probiotic microorganisms currently used to improve human health. We discovered that the majority of the investigated bacteria are able to catalyze the hydration reaction of the unsaturated fatty acids (UFAs). We evaluated their biocatalytic activity toward the three most common vegetable UFAs, namely oleic, linoleic, and linolenic acids. The whole-cell biotransformation experiments were performed using a fatty acid concentration of 3 g/L in anaerobic conditions. Through these means, we assessed that the main part of the investigated strains catalyzed the hydration reaction of UFAs with very high regio- and stereoselectivity. Our biotransformation reactions afforded almost exclusively 10-hydroxy fatty acid derivatives with the single exception of Lactobacillus acidophilus ATCC SD5212, which converted linoleic acid in a mixture of 13-hydroxy and 10-hydroxy derivatives. Oleic, linoleic, and linolenic acids were transformed into (R)-10-hydroxystearic acid, (S)-(12Z)-10-hydroxy-octadecenoic, and (S)-(12Z,15Z)-10-hydroxy-octadecadienoic acids, respectively, usually with very high enantiomeric purity (ee > 95%). It is worth noting that the biocatalytic capabilities of the thirteen investigated strains may change considerably from each other, both in terms of activity, stereoselectivity, and transformation yields. Lactobacillus rhamnosus ATCC 53103 and Lactobacillus plantarum 299 V proved to be the most versatile, being able to efficiently and selectively hydrate all three investigated fatty acids.

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Section: Resultsmentioning

confidence: 99%

Section: Determination Of the Absolute Configuration And Of The Opticmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Nevertheless, only few relevant exceptions to this general trend have been reported. An important example concerns some strains of Lactobacillus acidophilus [39][40][41] and Lactobacillus plantarum [42] that possess both 10and 13-hydratase activity, most likely due to the simultaneous activity of two different enzymes. Therefore, the whole-cell biotransformation of linolenic acid using the latter microorganisms can afford a mixture of (S)-(12Z)-10-hydroxy-octadecenoic acid (6), (S)-(9Z)-13-hydroxy-octadecenoic acid (8), and (10S,13S)-10,13-dihydroxy-octadecenoic acid (9).…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

The Fatty-Acid Hydratase Activity of the Most Common Probiotic Microorganisms

Serra¹,

Simeis²,

Castagna³

et al. 2020

Catalysts

View full text Add to dashboard Cite

show abstract

“…In 2014, Oh et al described a fatty acid hydratase from Stenotrophomonas nitritireducens, which converted 5.3 g L −1 linoleic acid and 0.93 g L −1 oleic acid [55]. The same group also utilized a linoleate 13-hydratase from Lactobacillus acidophilus to convert linoleic acid to hydroxy fatty acid via the use of recombinant whole cells, which produced 79 g L −1 within 3 h [56]. In 2015, Ogawa et al described a further gut bacterium (Lactobacillus acidophilus NTV001), which expresses a gene called FA-HY1 that is suitable to convert C18, as well as C20 and C22 unsaturated fatty acids [57].…”

Section: Application Of Fatty Acid Hydratase In Synthesis and Processmentioning

confidence: 99%

Fatty Acid Hydratases: Versatile Catalysts to Access Hydroxy Fatty Acids in Efficient Syntheses of Industrial Interest

Löwe

Gröger

2020

Catalysts

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The utilization of hydroxy fatty acids has gained more and more attention due to its applicability in many industrial building blocks that require it, for example, polymers or fragrances. Furthermore, hydroxy fatty acids are accessible from biorenewables, thus contributing to a more sustainable raw material basis for industrial chemicals. Therefore, a range of investigations were done on fatty acid hydratases (FAHs), since these enzymes catalyze the addition of water to an unsaturated fatty acid, thus providing an elegant route towards hydroxy-substituted fatty acids. Besides the discovery and characterization of fatty acid hydratases (FAHs), the design and optimization of syntheses with these enzymes, the implementation in elaborate cascades, and the improvement of these biocatalysts, by way of mutation in terms of the substrate scope, has been investigated. This mini-review focuses on the research done on process development using fatty acid hydratases as a catalyst. It is notable that biotransformations, running at impressive substrate loadings of up to 280 g L−1, have been realized. A further topic of this mini-review is the implementation of fatty acid hydratases in cascade reactions. In such cascades, fatty acid hydratases were, in particular, combined with alcohol dehydrogenases (ADH), Baeyer-Villiger monooxygenases (BVMO), transaminases (TA) and hydrolases, thus enabling access to a broad variety of molecules that are of industrial interest.

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Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes

et al. 2018

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The direct enantioselective addition of water to unactivated alkenes could simplify the synthesis of chiral alcohols and solve a long‐standing challenge in catalysis. Here we report that an engineered fatty acid hydratase can catalyze the asymmetric hydration of various terminal and internal alkenes. In the presence of a carboxylic acid decoy molecule for activation of the oleate hydratase from E. meningoseptica, asymmetric hydration of unactivated alkenes was achieved with up to 93 % conversion, excellent selectivity (>99 % ee, >95 % regioselectivity), and on a preparative scale.

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Production of 13S-hydroxy-9(Z)-octadecenoic acid from linoleic acid by whole recombinant cells expressing linoleate 13-hydratase from Lactobacillus acidophilus

Cited by 31 publications

References 39 publications

The Fatty-Acid Hydratase Activity of the Most Common Probiotic Microorganisms

The Fatty-Acid Hydratase Activity of the Most Common Probiotic Microorganisms

Fatty Acid Hydratases: Versatile Catalysts to Access Hydroxy Fatty Acids in Efficient Syntheses of Industrial Interest

Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes

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