PMID: 11344454May 10, 2001Paper

Efficient preparation of (R)-alpha-monobenzoyl glycerol by lipase catalyzed asymmetric esterification: optimization and operation in packed bed reactor

Biotechnology and Bioengineering
J H XuY Asano

Abstract

Optically active (R)-alpha-monobenzoyl glycerol (MBG) was synthesized by Candida antarctica lipase B (CHIRAZYME L-2) catalyzed asymmetric esterification of glycerol with benzoic anhydride in organic solvents. Various conditions, such as the type and composition of the organic solvent, water content of the system, reaction temperature, and concentrations of the substrates were systematically examined and optimized in screw-capped test tubes with respect to both the reaction rate and the enzyme selectivity. 1,4-Dioxane was found to be the best solvent and no additional water was needed for the system. The optimum temperature was around 30 degrees C, while the most suitable substrate concentrations were 100 mM each for glycerol and benzoic anhydride, respectively. However, when excessive anhydride (e.g., 200 mM) was used, the produced MBG could be further transformed into 1,3-dibenzoyl glycerol (DBG) by the same enzyme with a priority to (S)-MBG, resulting in a significant improvement of the product optical purity from ca. 50-70% e.e. Under optimal conditions (100 mM glycerol, 100-200 mM benzoic anhydride, dioxane, 25-30 degrees C), the enzymatic synthesis of (R)-MBG was successfully operated in a packed-bed reactor for about 1 we...Continue Reading

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Citations

Oct 11, 2003·Biotechnology Advances·R SharmaU C Banerjee
Feb 18, 2010·International Journal of Molecular Sciences·Zdenek Wimmer, Marie Zarevúcka
Jul 14, 2012·Chemical Communications : Chem Comm·Zachary X Giustra, Kian L Tan
Sep 20, 2017·Chembiochem : a European Journal of Chemical Biology·Ming-Min ZhengJian-He Xu
Jan 23, 2021·Biotechnology and Applied Biochemistry·Paula Jéssyca Morais LimaJosé Cleiton Sousa Dos Santos
Oct 17, 2008·Chemical Reviews·Yuguo ZhengYinchu Shen

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