Lipase-catalyzed chemoselective aminolysis of various aminoalcohols with fatty acids

Couturier, Lucie; Taupin, Delphine; Yvergnaux, Florent

doi:10.1016/j.molcatb.2008.04.010

Cited by 32 publications

(20 citation statements)

References 27 publications

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“…In order to overcome these disadvantages, several studies focused on developing enzymatic syntheses of pseudo-ceramides through immobilized lipase-catalyzed acylation or transacylation reactions carried out in an organic solvent or in a solvent-free system [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Continuous lipase-catalyzed production of pseudo-ceramides in a packed-bed bioreactor

Joubioux

Bridiau

Sanekli

et al. 2014

Journal of Molecular Catalysis B: Enzymatic

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Ceramides are spingolipid compounds that are very attractive as active components in both the pharmaceutical and the cosmetic industries. In this study, the synthesis of ceramide analogs, the so-called pseudo-ceramides, was carried out using for the first time a two-step continuous enzymatic process with immobilized Candida antarctica lipase B (Novozym ® 435) in a packed-bed bioreactor. The first step involved the selective N-acylation of 3-amino-1,2-propanediol using stearic acid as the first acyl donor (i). This was followed by the selective O-acylation of the N-stearyl 3-amino-1,2-propanediol synthesized in the first step, with myristic acid as the second acyl donor, to produce a N,O-diacyl 3-amino-1,2propanediol-type pseudo-ceramide, namely 1-O-myristyl,3-N-stearyl 3-amino-1,2propanediol (ii). The process was first optimized by evaluating the influences of three factors: feed flow rate, quantity of biocatalyst and substrate concentration. Under optimal conditions an amide synthesis yield of 92% and a satisfying production rate of almost 3.15 mmol h-1

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Section: Introductionmentioning

confidence: 99%

Continuous lipase-catalyzed production of pseudo-ceramides in a packed-bed bioreactor

Joubioux

Bridiau

Sanekli

et al. 2014

Journal of Molecular Catalysis B: Enzymatic

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“…22 The aminolysis of linoleyl ethyl ester with ethanolamine, catalyzed by CAL, in a solvent free system produced the linoleylethanolamide only in 24% yield in 20 h including the presence of the unwanted o -acylation product. 23 While these examples show the use of lipases for the amidation of esters, there is limited reported work on the use of lipases as a direct method for the synthesis of biologically active NAEs with regard to functional group sensitivity common in the synthesis of modified fatty acid moieties. We have thus focused our efforts on the synthesis of biologically active NAEs with immobilized CAL from methyl esters and various amines.…”

mentioning

confidence: 99%

Enzymatic synthesis of N-acylethanolamines: direct method for the aminolysis of esters

Whitten

Makriyannis

Vadivel

2012

Tetrahedron Letters

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“…For this synthesis, we suggested an original biotechnological solvent‐free process (Fig. 6) [29, 30].…”

Section: Resultsmentioning

confidence: 99%

Combined structural and biological activities for new polyunsaturated fatty derivatives obtained by biotechnological process

Couturier¹,

Yvergnaux²

2009

Intern J of Cosmetic Sci

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The objective of this study is to demonstrate the use of new polyunsaturated fatty derivatives for cutaneous applications. These new compounds present an analogue structure of cutaneous lipid, stabilize the polyunsaturated fatty acids (face to oxidation) and demonstrate specific biological activities. Three molecules described are Omega 6 fatty acid stabilized compound (O6FASC), the O3FASC and the O9FASC. The derivatives are synthesized via the same biotechnological process. This work describes the choice of final structure, the design of the biotechnological process and the free solvent enzymatic synthesis used for the synthesis of these three cutaneous lipid analogues. The restructuring effect of such analogues has been demonstrated with an in vivo study on volunteers. The stabilization of the O3FASC and O6FASC, and the biological activities of these three compounds are presented. The O6FASC shows very good results in anti-inflammatory effects; the O3FASC has anti-stress activities, whereas the O9FASC presents interesting results in improving elasticity and firmness. All these activity tests are presented in this work.

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Lipase-catalyzed chemoselective aminolysis of various aminoalcohols with fatty acids

Cited by 32 publications

References 27 publications

Continuous lipase-catalyzed production of pseudo-ceramides in a packed-bed bioreactor

Continuous lipase-catalyzed production of pseudo-ceramides in a packed-bed bioreactor

Enzymatic synthesis of N-acylethanolamines: direct method for the aminolysis of esters

Combined structural and biological activities for new polyunsaturated fatty derivatives obtained by biotechnological process

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