Direct Biotransformation of Nonanoic Acid and Its Esters to Azelaic Acid by Whole Cell Biocatalyst of <i>Candida tropicalis</i>

Kim, Jiyoung; Jun, Min-Woo; Seong, Yeong-Je; Ahn, Jungoh; Park, Yong-Cheol

doi:10.1021/acssuschemeng.9b04723

Cited by 11 publications

(6 citation statements)

References 35 publications

(98 reference statements)

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“…The direct biotransformation of nonanoic acid and its ester to azelaic acid was recently proposed using Candida tropicalis as a whole-cell biocatalyst. The biotransformation by continuous feeding of pure nonanoic acid, with the addition of inducer (nonane) and glucose, resulted in 30 g/L azelaic acid production with 0.3 g/L-h productivity and 90% molar yield [174].…”

Section: Adipic Acidmentioning

confidence: 99%

Contribution of Fermentation Technology to Building Blocks for Renewable Plastics

Lomwongsopon

Varrone

2022

Fermentation

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Large-scale worldwide production of plastics requires the use of large quantities of fossil fuels, leading to a negative impact on the environment. If the production of plastic continues to increase at the current rate, the industry will account for one fifth of global oil use by 2050. Bioplastics currently represent less than one percent of total plastic produced, but they are expected to increase in the coming years, due to rising demand. The usage of bioplastics would allow the dependence on fossil fuels to be reduced and could represent an opportunity to add some interesting functionalities to the materials. Moreover, the plastics derived from bio-based resources are more carbon-neutral and their manufacture generates a lower amount of greenhouse gasses. The substitution of conventional plastic with renewable plastic will therefore promote a more sustainable economy, society, and environment. Consequently, more and more studies have been focusing on the production of interesting bio-based building blocks for bioplastics. However, a coherent review of the contribution of fermentation technology to a more sustainable plastic production is yet to be carried out. Here, we present the recent advancement in bioplastic production and describe the possible integration of bio-based monomers as renewable precursors. Representative examples of both published and commercial fermentation processes are discussed.

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Section: Adipic Acidmentioning

confidence: 99%

Contribution of Fermentation Technology to Building Blocks for Renewable Plastics

Lomwongsopon

Varrone

2022

Fermentation

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“…It was noted that it is produced naturally by Pityrosporum ovale, a yeast that lives on skin [29,30]. Also, Candida tropicalis, a ubiquitous yeast, is a known producer of azelaic acid [31]. This pointed towards the involvement of microorganisms in the formation of DiFAs, which are likely more present in head tissue than in fillet.…”

Section: Concentrations Of Dicarboxylated Fatty Acids (Difa-dimes) In Tilapia Head Tissuementioning

confidence: 99%

Identification and quantification of dicarboxylic fatty acids in head tissue of farmed Nile tilapia (Oreochromis niloticus)

Lehnert

Rashid

Barman

et al. 2021

Eur Food Res Technol

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Nile tilapia (Oreochromis niloticus) was grown in Bangladesh with four different feeding treatments as part of a project that aims to produce fish in a cost-effective way for low-income consumers in developing countries. Fillet and head tissue was analysed because both tissues were destined for human consumption. Gas chromatography with mass spectrometry (GC/MS) analyses of transesterified fatty acid methyl ester extracts indicated the presence of ~ 50 fatty acids. Major fatty acids in fillet and head tissue were palmitic acid and oleic acid. Both linoleic acid and polyunsaturated fatty acids with three or more double bonds were presented in quantities > 10% of total fatty acids in fillet, but lower in head tissue. Erucic acid levels were below the newly proposed tolerable daily intake in the European Union, based on the consumption of 200 g fillet per day. Moreover, further analysis produced evidence for the presence of the dicarboxylic fatty acid azelaic acid (nonanedioic acid, Di9:0) in head tissue. To verify this uncommon finding, countercurrent chromatography was used to isolate Di9:0 and other dicarboxylic acids from a technical standard followed by its quantification. Di9:0 contributed to 0.4–1.3% of the fatty acid profile in head tissue, but was not detected in fillet. Fish fed with increasing quantities of flaxseed indicated that linoleic acid was the likely precursor of Di9:0 in the head tissue samples.

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“…A multi-enzymatic one-pot reaction was developed to convert linoleic acid into azelaic acid by combining a 9S-lipoxygenase and 9/13-hydroperoxide lyase to obtain 9-oxononanoic acid submitted to the final oxidation to acid 2 catalyzed by an alcohol dehydrogenase. In 2019 the capability of Candida tropicalis ATCC20962 to transform nonanoic acid and its esters into azelaic acid 2 with the aid of nonane addition and continuous glucose supply [24] was investigated, to improve the production yield of diacid 2 obtained in the ozonolysis process of oleic acid.…”

Section: Introductionmentioning

confidence: 99%

Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route

Brenna

Colombo

Lecce³

et al. 2020

Molecules

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A chemo-enzymatic approach for the conversion of oleic acid into azelaic and pelargonic acid is herein described. It represents a sustainable alternative to ozonolysis, currently employed at the industrial scale to perform the reaction. Azelaic acid is produced in high chemical purity in 44% isolation yield after three steps, avoiding column chromatography purifications. In the first step, the lipase-mediated generation of peroleic acid in the presence of 35% H2O2 is employed for the self-epoxidation of the unsaturated acid to the corresponding oxirane derivative. This intermediate is submitted to in situ acid-catalyzed opening, to afford 9,10-dihydroxystearic acid, which readily crystallizes from the reaction medium. The chemical oxidation of the diol derivative, using atmospheric oxygen as a stoichiometric oxidant with catalytic quantities of Fe(NO3)3∙9∙H2O, (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO), and NaCl, affords 9,10-dioxostearic acid which is cleaved by the action of 35% H2O2 in mild conditions, without requiring any catalyst, to give pelargonic and azelaic acid.

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Direct Biotransformation of Nonanoic Acid and Its Esters to Azelaic Acid by Whole Cell Biocatalyst of Candida tropicalis

Cited by 11 publications

References 35 publications

Contribution of Fermentation Technology to Building Blocks for Renewable Plastics

Contribution of Fermentation Technology to Building Blocks for Renewable Plastics

Identification and quantification of dicarboxylic fatty acids in head tissue of farmed Nile tilapia (Oreochromis niloticus)

Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route

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