Improved racemate resolution of pentan-2-ol and trans-(Z)-cyclooct-5-ene-1,2-diol by lipase catalysis

• Published in: Journal of Biotechnology
• Main Authors: Graber, Marianne, Rouillard, Hervé, Delatouche, Régis, Fniter, Najla, Belkhiria, Belsem, Bonnet, Antoine, Domon, Lisiane, Thiéry, Valérie
• Other Authors: LIttoral ENvironnement et Sociétés - UMR 7266 (LIENSs), Institut national des sciences de l'Univers (INSU - CNRS)-La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS), ANR-08-CP2D-0010,EXPENANTIO,Vers une voie durable pour la synthèse de molécules chirales: approches expérimentales et théoriques innovantes pour la compréhension des bases moléculaires de l'énantiosélectivité des lipases et des estérases - Towards green synthesis of chiral molecules(2008)
• Format: Article in Journal/Newspaper
• Language: English
• Published: HAL CCSD 2016
• Subjects: [SDV.BIO]Life Sciences [q-bio]/Biotechnology; [CHIM]Chemical Sciences; Antarc*
• Online Access: https://hal.science/hal-01432549; https://hal.science/hal-01432549/document; https://hal.science/hal-01432549/file/Revised%20Manuscrip%20r%C3%A9visions%20accept%C3%A9est.pdf; https://hal.science/hal-01432549/file/Captions%20to%20Figures.pdf; https://hal.science/hal-01432549/file/Figure%201.pdf; https://hal.science/hal-01432549/file/Figure%202.pdf; https://hal.science/hal-01432549/file/Figure%203.pdf; https://hal.science/hal-01432549/file/Figure%204.pdf; https://hal.science/hal-01432549/file/Figure%205.pdf; https://hal.science/hal-01432549/file/Figure%206.pdf; https://hal.science/hal-01432549/file/Scheme%201.pdf; https://doi.org/10.1016/j.jbiotec.2016.09.010

International audience Lipases are important catalysts in chiral synthesis due to their wide substrate recognition combined witha high stereoselectivity. We demonstrate here that the state, free or immobilized, of Candida antarcticalipase B (CaLB) affects enantioselectivity and also alters the temperature dependancy of the enzyme. Thisindicates that CaLB undergoes various conformations induced by its interaction with the different immo-bilization supports studied. Molecular imprinting experiments, using immobilized enzyme co-dried withmimic substrate molecules, enhanced the enantiomeric ratio two-fold or three-fold, depending on theimmobilization support. The structure of the acyl donor has a pronounced effect on CaLB catalyzed res-olution, due to the proximity of the acyl and alcohol moieties during catalysis. When the acylation ofpentan-2-ol was examined, we found that the 3C methyl propanoate donor afforded the highest resolu-tion. Trans-(Z)-cyclooct-5-en-1,2-diol was used as a model racemic substrate to study the ability of lipaseto catalyze the resolution of difunctionalized compounds. There was a clear enhancement in the enan-tiomer selectivity of the biotransformation of the diol when vinyl butanoate is used as the acyl donor. Theconversion and enantiomeric excess of (1R,2R)-monoacetates were enhanced, using immobilized CaLB,when the chain length of the donors increased from C2 to C4.