Biotransformations with Lipases

Kazlauskas, Romas J.; Bornscheuer, Uwe T.

doi:10.1002/9783527620999.ch3h

Cited by 57 publications

(25 citation statements)

References 1,030 publications

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“…Production of structured lipids by lipase-catalyzed interesterification has recently attracted much attention from both academia and industry (1)(2)(3)(4). The most exciting part of the technology is to exploit the regiospecificity of the lipases to produce tailor-made fats, which can be targeted for special nutritional requirements.…”

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confidence: 99%

Purification of specific structured lipids by distillation: Effects on acyl migration

Skands

Adler‐Nissen

2001

J Americ Oil Chem Soc

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The cause and effects of acyl migration during the purification of specific structured lipids by distillation were studied in a conventional batch deodorizer with stripping steam. The mixture of specific structured lipids produced by lipase-catalyzed acidolysis between rapeseed oil and capric acid contained a large amount of free fatty acids and a small amount of partial acylglycerols besides triacylglycerols. Therefore, the effect of steam, free fatty acids, diacylglycerols, and monoacylglycerols on acyl migration was studied in a palm oil midfraction model. The results showed that all these factors influenced the rate of acyl migration, and their combinations made the effect more severe. However, diacylglycerols were found to be the main reason for acyl migration. In the distillation of the specific structured lipid product mixture, distillation temperature and time were the main factors to determine the degree of acyl migration and the extent of separation of free fatty acids. The results indicate that more efficient separation technology should be used to improve the quality of the purified structured lipids. In order to reduce the distillation temperature, vacuum should be made as low as possible with more effective pumps. To reduce the distillation time, thin-film principle in a packed column should be used, or other more efficient distillation techniques such as molecular distillation or short-path distillation should be exploited.Paper no. J9715 in JAOCS 78, 715-718 (July 2001).KEY WORDS: Acyl migration, batch distillation, lipase-catalyzed acidolysis, specific structured lipids.Production of structured lipids by lipase-catalyzed interesterification has recently attracted much attention from both academia and industry (1-4). The most exciting part of the technology is to exploit the regiospecificity of the lipases to produce tailor-made fats, which can be targeted for special nutritional requirements. The normal production method is to carry out an acidolysis reaction catalyzed by a lipase. The resulting product is a mixture of the expected structured lipids and free fatty acids (FFA), together with small amounts of partial acylglycerols. The purification of structured lipids is usually performed by distillation.Acyl migration leads to nonspecific by-products. It occurs during lipase-catalyzed interesterification and is affected by factors such as water content, reaction time, reaction temperature, enzyme load, reactor type, and reaction system (5,6). To minimize acyl migration, it is necessary to choose the right reactor and to optimize the reaction system.Acyl migration is also observed during the purification of specific structured lipids (SSL) by conventional distillation (7). It can be seen also that acyl migration occurs to a greater extent during the purification stage in the conventional batch deodorizer than in the reaction stage. No information so far has elucidated the phenomenon. This problem cannot be neglected with respect to the production of high-quality structured lipids.In this study, tw...

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confidence: 99%

Purification of specific structured lipids by distillation: Effects on acyl migration

Skands

Adler‐Nissen

2001

J Americ Oil Chem Soc

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“…The mixture was allowed to warm up to room temperature and was stirred until TLC indicated complete consumption of the starting material. The reaction was quenched with saturated aqueous NH 4 Cl solution (11.5 mL/ mmol 17), the organic layer separated, and the aqueous layer extracted with CH 2 Cl 2 . The combined organic fractions were washed with saturated aqueous bicarbonate solution and brine, dried over MgSO 4 , filtered and the solvent removed under reduced pressure.…”

Section: General Procedures For the Caprylation And Caproylation Of Almentioning

confidence: 99%

Kinetic Enzymatic Resolution of Cyclopropane Derivatives

et al. 2003

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Abstract:The kinetic enzymatic resolution of various cyclopropane derivatives was systematically investigated. The study focused on synthetically useful cyclopropylmethanols (e.g., 18a/j or 19a/j) as well as some rarely investigated cyclopropanols (e.g., 24/25 or 27). The combination of enantioselective catalytic or diastereoselective synthesis of enantiomerically enriched compounds with enzymatic approaches ultimately led to the most convenient route to enantiomerically pure starting materials. Again, this was especially proven for the synthesis of cyclopropanols 18a/j and 19a/j. Key to the successful investigation was to rigorously establish an analytical tool for the analysis of enantiomeric composition of reaction mixtures.

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“…Spectra were obtained in deuterated methanol with tetramethylsilane (TMS) as reference in tubes with a diameter of 5 mm. Examples of chemical shifts in the 1 H-NMR spectra of fatty alcohol esters of carbohydrate acids: dodecyl quinate, δ ppm 0.9 (t, CH 3 …”

Section: Nmr Spectroscopymentioning

confidence: 99%

“…3.1.1.3) to catalyze (trans)esterification reactions in organic media is known and well documented [1][2][3]. Examples of lipase-catalyzed esterification reactions are numerous and various bibliographic reviews have been published on different topics such as oils and fats restructuring [4], racemic mixture resolution [5] or surfactant synthesis [6].…”

Section: Introductionmentioning

confidence: 99%

Lipase-catalyzed synthesis of quinate and glucuronate fatty esters

Villeneuve¹,

Hills²,

Bachain³

et al. 2002

Eur. J. Lipid Sci. Technol.

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Lipase-catalyzed synthesis of quinate and glucuronate fatty estersThe lipase-catalyzed synthesis of fatty alcohol esters of quinic and glucuronic acid was investigated. The results showed that although a direct esterification process was possible, a strategy involving short-chain alkyl ester intermediates was advantageous. 2-Methyl-2-butanol was chosen as solvent and parameters such as substrate ratios and concentrations were optimized. Octyl, decyl and hexadecyl esters of quinic and glucuronic acids could be obtained with this process. However, reaction rates were rather slow and it could be shown that the completely chemically catalyzed synthesis of the same products using ion exchange resins was advantageous.

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Biotransformations with Lipases

Cited by 57 publications

References 1,030 publications

Purification of specific structured lipids by distillation: Effects on acyl migration

Purification of specific structured lipids by distillation: Effects on acyl migration

Kinetic Enzymatic Resolution of Cyclopropane Derivatives

Lipase-catalyzed synthesis of quinate and glucuronate fatty esters

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