Specificity of Candida antarctica lipase B (SP 435) in the presence of lipase A in a double enantioselective transesterification

Theil, Fritz; Björkling, Fredrik

doi:10.1007/bf00138549

Cited by 13 publications

(1 citation statement)

References 12 publications

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“…This might be related to the fitting of the substrate in the enzyme-active site. The latter can indeed, be divided into two pockets, an acid side and an alcohol side, corresponding to both ester-moiety positions during catalysis (Theil and Bjorkling, 1993;Uppenberg et al, 1995). The narrowness of the alcohol channel has been reported to be responsible for C.antarctica lipase stereospecificity for secondary alcohols (Orrenius et al, 1995).…”

Section: Influence Of Acyl Donormentioning

confidence: 99%

Enzymatic synthesis of α‐butylglucoside lactate: A new α‐hydroxy acid derivative

Bousquet

Willemot

Monsan

et al. 1999

Biotech & Bioengineering

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An α‐hydroxy acid derivative, α‐butylglucoside lactate, was successfully prepared by enzymatic transesterification of α‐butylglucoside with a lactate alkyl ester in a non‐aqueous medium using immobilized lipase as biocatalyst. Ester synthesis in organic solvent was optimized. Solvent choice was made on the basis of substrate solubility and enzyme stability in the medium. A solvent‐free reaction using butyllactate as lactate donor led to the highest yields. In the presence of 0.5M αbutylglucoside and 100 g/L Novozym®, a 67 % yield could be obtained within 40 h at 50°C. However, the presence of butanol by‐product limited the reaction to a maximum that could not be exceeded in closed systems. The elimination of the alcohol under reduced pressure resulted in the complete equilibrium shift of the transesterification reaction in favor of synthesis; below 15 mbars, more than 95% of 0.5M α‐butylglucoside could be converted within 30 h. Moreover, simultaneous evaporation of water allowed hydrolysis of butyllactate to be eliminated. Consequently, a very high α‐butylglucoside lactate concentration (170 g/) could be obtained in a single batch reaction. A single purification procedure, consisting of butyllactate extraction with hexane, enabled the product to be obtained at a purity above 95% (w/w). 1H and 13C NMR analysis later demonstrated that lactic acid was exclusively grafted onto the primary hydroxyl group of αbutylglucoside. © 1999 John Wiley & Sons, Inc. Biotechnol Bioeng 62: 225–234, 1999.

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Section: Influence Of Acyl Donormentioning

confidence: 99%

Enzymatic synthesis of α‐butylglucoside lactate: A new α‐hydroxy acid derivative

Bousquet

Willemot

Monsan

et al. 1999

Biotech & Bioengineering

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Lipase‐Catalyzed Doubly Enantioselective Ring‐Opening Resolution between Alcohols and Lactones: Synthesis of Chiral Hydroxyl Esters with Two Stereogenic Centers

Xia

Cheng

et al. 2014

ChemCatChem

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A novel lipase B from Candida antarctica‐catalyzed doubly enantioselective ring‐opening resolution between racemic alcohols and lactones was developed. By using this strategy, three optically pure compounds including hydroxyl esters with two stereogenic centers and recovered alcohols and lactones were obtained simultaneously in high yields and ee. This process was used for the resolution of various racemic alcohols with different substituent groups and lactones with different ring sizes (four‐ and seven‐ membered lactones). The scale‐up experiments were also successful. Moreover, molecular docking was performed to explain the molecular basis of this doubly enantioselective ring‐opening resolution. As an attractive and efficient strategy, lipase‐catalyzed doubly enantioselective ring‐opening resolution will be widely used in the synthesis of optically pure hydroxyl esters with two stereogenic centers.

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Synthesis of mono- and dioleylglycerols using an immobilized lipase

Pastor

Otero

1995

Appl Biochem Biotechnol

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Specificity of Candida antarctica lipase B (SP 435) in the presence of lipase A in a double enantioselective transesterification

Cited by 13 publications

References 12 publications

Enzymatic synthesis of α‐butylglucoside lactate: A new α‐hydroxy acid derivative

Enzymatic synthesis of α‐butylglucoside lactate: A new α‐hydroxy acid derivative

Lipase‐Catalyzed Doubly Enantioselective Ring‐Opening Resolution between Alcohols and Lactones: Synthesis of Chiral Hydroxyl Esters with Two Stereogenic Centers

Synthesis of mono- and dioleylglycerols using an immobilized lipase

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