Effect of decanoic acid and 10-hydroxydecanoic acid on the biotransformation of methyl decanoate to sebacic acid

Abstract

Biotransformation of fatty acid methyl esters to dicarboxylic acids has attracted much attention in recent years; however, reports of sebacic acid production using such biotransformation remain few. The toxicity of decanoic acid is the main challenge for this process. Decane induction has been reported to be essential to activate the enzymes involved in the α,ω-oxidation pathway before initiating the biotransformation of methyl decanoate to sebacic acid. However, we observed the accumulation of intermediates (decanoic acid and 10-hydroxydecanoic acid) during the induction period. In this study, we examined the effects of these intermediates on the biotransformation process. The presence of decanoic acid, even at a low concentration (0.2 g/L), inhibited the transformation of 10-hydroxydecanoic acid to sebacic acid. Moreover, about 24–32% reduction in the decanoic acid oxidation was observed in the presence of 0.5–1.5 g/L 10-hydroxydecanoic acid. To eliminate these inhibitory effects, we applied substrate-limiting conditions during the decane induction process, which eliminated the accumulation of decanoic acid. Although the productivity of sebacic acid (34.5 ± 1.10 g/L) was improved, by 28% over that achieved using the previously methods, after 54 h, the accumulation of 10-hydroxydecanoic acid was still detected. The accumulation of 10-hydroxydecanoic acid even under the decane limiting conditions could be an evidence that oxidation of 10-hydroxydecanoic acid could be the rate-limiting step in this process. The improvement of this reaction should be an important objective for further development of the production of sebacic acid using biotransformation.Electronic supplementary materialThe online version of this article (10.1186/s13568-018-0605-4) contains supplementary material, which is available to authorized users.

Development of a promising microbial platform for the production of dicarboxylic acids from biorenewable resources

“…In C. tropicalis , a well-known DCA-producing yeast, the fermentation process for DCA production has already been optimized [ 2 , 33 , 34 ]. The fermentation for DCA production is divided into growth and conversion stages, where the medium pH greatly affects fatty acid and DCA solubility, DCA excretion and cell viability [ 11 , 34 ]. During the conversion stage, acidic conditions (= pH 5.8) steadily promoted the cell growth, but DCA precipitates were formed and interfered with the process [ 35 ].…”

“…DCA conversion is initiated by cytochrome P450 monooxygenase (CYP); members of the CYP family are alkane-inducible in alkane-assimilating yeasts [ 37 – 39 ]. In C. tropicalis , the addition of methyl decanoate without the pre-activation of ω-oxidation resulted in the accumulation of decanoic acid and directly affected cell viability [ 11 ]. Thus, prior to methyl laurate addition, 1% (v/v) dodecane of the culture was added to pre-activate the ω-oxidation pathway of W. sorbophila .…”

“…In particular, medium-chain fatty acids (chain length ≤ 12) are highly toxic compounds, which cause cell membrane stress, disruption of the electron transport system, acidification of the cytoplasm, and production of reactive oxygen species [ 9 , 10 ]. Medium-chain fatty acid methyl esters, such as methyl decanoate and methyl laurate, are hydrolyzed by extracellular lipases or esterases during the conversion phase and the resulting fatty acids cause cellular toxicity [ 11 ]. Because of its toxicity, various concentrations of DCA are produced, depending on the carbon chain length of fatty acids or that of methyl esters (Table 1 ).…”

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

“…A C. tropicalis mutant was able to convert methyl decanoate to 34.5 g/L sebacic acid (C 10 -DCA) in a fed-batch type of biotransformation . It was announced that a commercial plant had been constructed to produce dodecanedioic acid (C 12 -DCA) from the 12 carbon fatty acid or alkane by Candida sp .…”

Biosynthesis of Medium-Chain ω-Hydroxy Fatty Acids by AlkBGT of Pseudomonas putida GPo1 With Native FadL in Engineered Escherichia coli

“…ω-Hydroxydecanoic acid can be further derivatized to sebacic acid, which is an important precursor in the production of nylon and polyamides (PAs), primarily 4,10-PA and 5,10-PA (Bowen et al, 2016). ω-Hydroxydodecanoic acid has the potential to enable commercially relevant production of C12 α, ω-DCA, a valuable precursor of nylon-6,12 (Sugiharto et al, 2018).…”