Simple Preparation of Highly Pure Monomeric <i>ω</i>-Hydroxycarboxylic Acids

Stephan, Michel; Mohar, Barbara

doi:10.1021/op0502046

Cited by 15 publications

(13 citation statements)

References 17 publications

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“…Chemically, ω-OHFAs can be obtained by cross-metathesis of unsaturated fatty acid esters, followed by the hydroformylation and hydrogenation of the carbonyl group ( Warwel et al ., 1992 ; Metzger and Bornscheuer, 2006 ) or by the reduction of α,ω-DCAs ( Yokota and Watanabe, 1992 ). Dicarboxylic acids can be prepared by the catalytic ring opening of lactones and cyclic ketones ( Cotarca and Nardelli, 1999 ; Stephan and Mohar, 2006 ). However, the synthesis of ω-OHFAs or α,ω-DCAs via the terminal oxygenation of saturated or unsaturated fatty acids is not practised in chemocatalysis, as selectivity and controlled reactivity in C-H oxygenation reactions are difficult to achieve.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of ω‐hydroxy dodecanoic acid based on an engineered CYP153A fusion construct

Scheps

Malca

Richter

et al. 2013

Microbial Biotechnology

104

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A bacterial P450 monooxygenase-based whole cell biocatalyst using Escherichia coli has been applied in the production of ω-hydroxy dodecanoic acid from dodecanoic acid (C12-FA) or the corresponding methyl ester. We have constructed and purified a chimeric protein where the fusion of the monooxygenase CYP153A from Marinobacter aquaeloei to the reductase domain of P450 BM3 from Bacillus megaterium ensures optimal protein expression and efficient electron coupling. The chimera was demonstrated to be functional and three times more efficient than other sets of redox components evaluated. The established fusion protein (CYP153AM. aq.-CPR) was used for the hydroxylation of C12-FA in in vivo studies. These experiments yielded 1.2 g l–1 ω-hydroxy dodecanoic from 10 g l–1 C12-FA with high regioselectivity (> 95%) for the terminal position. As a second strategy, we utilized C12-FA methyl ester as substrate in a two-phase system (5:1 aqueous/organic phase) configuration to overcome low substrate solubility and product toxicity by continuous extraction. The biocatalytic system was further improved with the coexpression of an additional outer membrane transport system (AlkL) to increase the substrate transfer into the cell, resulting in the production of 4 g l–1 ω-hydroxy dodecanoic acid. We further summarized the most important aspects of the whole-cell process and thereupon discuss the limits of the applied oxygenation reactions referring to hydrogen peroxide, acetate and P450 concentrations that impact the efficiency of the production host negatively.

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Section: Introductionmentioning

confidence: 99%

Synthesis of ω‐hydroxy dodecanoic acid based on an engineered CYP153A fusion construct

Scheps

Malca

Richter

et al. 2013

Microbial Biotechnology

104

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“…R f 0.10 (petroleum ether-methyl tert-butyl ether, 3 : 1). The 1 Н and 13 С NMR spectra are identical to those described in [37].…”

Section: Methodsmentioning

confidence: 73%

One-pot ozonolytic synthesis of acyclic α,ω-bifunctional compounds from methyl 10-undecenoate and 10-undecen-1-ol

et al. 2015

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Transformations of peroxy products formed by ozonolysis of undecylenic acid derivatives (methyl ester and hydride reduction product, 10-undecen-1-ol) in various protic and aprotic solvents (МеОН, Pr i OH, tetrahydrofuran, 1 : 5 AcOH-CH 2 Cl 2 mixture), occurring under the action of such reductants as hydroxylamine and semicarbazide hydrochlorides, were studied. These reductants exhibit high performance and in some cases high chemoselectivity, which allowed the development of a number of one-pot procedures for the synthesis of acyclic α,ω-bifunctional compounds, the majority of which are widely used in medicine, perfumery, cosmetics, engineering, and chemical industry, e.g., as block synthons in targeted organic synthesis.

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“…A large number of synthetic routes for the production of x-HFA have been described in the literature (2). To reliably provide x-HFA as a future raw material for the industrial chemical sector, it is necessary to develop large-scale, high-yield production systems for a wider range of x-HFA (production of plastics, adhesives, and surface coatings).…”

Section: Synthetic Production Of X-hydroxylated Fatty Acidsmentioning

confidence: 99%

Functionality at the end of a fatty acid chain – chemical and biological routes to ω‐hydroxylated fatty acids

2009

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Hydroxylated fatty acids are valuable compounds in the chemical industry, being used in various products. ω‐Hydroxylated fatty acids are versatile oleochemicals that can be used in polyester and polyamide production. Although a significant number of conventional synthetic chemistry production routes have been developed for ω‐hydroxy acids, considerable challenge relates to their production in price‐competitive, renewable, and sustainable production systems. The development and utilisation of biological systems for ω‐hydroxy acid production may allow the transition of these compounds from specialty chemical to commodity material. The viability of biological routes to ω‐hydroxylated fatty acids is dependent on the identification of enzymes and systems capable of such modifications. Cytochrome P450 monooxygenases are currently the only characterised enzymes known to ω‐hydroxylate fatty acids and yeast provides valuable systems to perform the ω‐hydroxylation biotransformations.

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Simple Preparation of Highly Pure Monomeric ω-Hydroxycarboxylic Acids

Cited by 15 publications

References 17 publications

Synthesis of ω‐hydroxy dodecanoic acid based on an engineered CYP153A fusion construct

Synthesis of ω‐hydroxy dodecanoic acid based on an engineered CYP153A fusion construct

One-pot ozonolytic synthesis of acyclic α,ω-bifunctional compounds from methyl 10-undecenoate and 10-undecen-1-ol

Functionality at the end of a fatty acid chain – chemical and biological routes to ω‐hydroxylated fatty acids

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