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Thierry Maugard – One of the best experts on this subject based on the ideXlab platform.

  • Kinetic study of 2-butanol O-Acylation and sec-butylamine N-Acylation catalyzed by Candida antarctica lipase B
    Journal of Molecular Catalysis B: Enzymatic, 2011
    Co-Authors: Florian Le Joubioux, A. Oussama, Nicolas Bridiau, Marianne Graber, Thierry Maugard
    Abstract:

    The aim of this work was to study the differential behavior shown by Candida antarctica lipase B during the O-Acylation and N-Acylation of monofunctional alcohols and monofunctional amines. To achieve this, 2-butanol and sec-butylamine were used as model molecules. Yields, kinetics and enantioselectivity were studied for both reactions. Although a steady-state ordered ternary complex bi-bi mechanism was obtained for the O-Acylation of 2- butanol, a ping-pong bi-bi mechanism was obtained for the N-Acylation in case of low sec- butylamine concentrations. The values of apparent kinetics parameters were calculated: the enantiomeric ratios (E) were evaluated and confirmed the preference of Candida antarctica lipase B for the (R)-enantiomer, which was consistent with the literature. The nantioselectivity was calculated for the alcohol (E ≈ 3.17) and for the amine (E ≈ 1.34). Concerning the O-Acylation, the yields were found to be very similar for both enantiomers R and S. However, both initial rates and yields of the (R)-enantiomer N-Acylation were higher than those of the (S)-enantiomer. In the last part of our study, the chemoselectivity of Candida antarctica lipase B was evaluated, showing that Candida antarctica lipase B was a chemoselective enzyme that preferentially catalyzed the O-Acylation to the detriment of the N-Acylation (C ≈ 92, for the selective Acylation of (R)-enantiomers). These results provide new insights for the synthesis of products issued from the selective Acylation of multifunctional substrates such as amino-alcohols.

  • Kinetic study of 2-butanol O-Acylation and sec-butylamine N-Acylation catalyzed by Candida antarctica lipase B
    Journal of Molecular Catalysis B: Enzymatic, 2011
    Co-Authors: Florian Le Joubioux, Nicolas Bridiau, Marianne Graber, Oussama Achour, Thierry Maugard
    Abstract:

    The aim of this work was to study the differential behavior shown by Candida antarctica lipase B during the O-Acylation and N-Acylation of monofunctional alcohols and monofunctional amines. To achieve this, 2-butanol and sec-butylamine were used as model molecules. Yields, kinetics and enantioselectivity were studied for both reactions. Although a steady-state ordered ternary complex bi-bi mechanism was obtained for the O-Acylation of 2-butanol, a ping-pong bi-bi mechanism was obtained for the N-Acylation in case of low sec-butylamine concentrations. The values of apparent kinetic parameters were calculated: the enantiomeric ratios (E) were evaluated and confirmed the preference of C. antarctica lipase B for the (R)-enantiomer, which was consistent with the literature. The enantioselectivity was calculated for the alcohol (E ≈ 3.17) and for the amine (E ≈ 1.34). Concerning the O-Acylation, the yields were found to be very similar for both enantiomers R and S. However, both initial rates and yields of the (R)-enantiomer N-Acylation were higher than those of the (S)-enantiomer. In the last part of our study, the chemoselectivity of C. antarctica lipase B was evaluated, showing that C. antarctica lipase B was a chemoselective enzyme that preferentially catalyzed the O-Acylation to the detriment of the N-Acylation (C ≈ 92, for the selective Acylation of (R)-enantiomers). These results provide new insights for the synthesis of products issued from the selective Acylation of multifunctional substrates such as amino-alcohols.

  • Kinetic study of 2-butanol O-Acylation and sec-butylamine N-Acylation catalyzed by Candida antarctica lipase B
    Journal of Molecular Catalysis B: Enzymatic, 2011
    Co-Authors: Florian Le Joubioux, Nicolas Bridiau, Marianne Graber, Oussama Achour, Thierry Maugard
    Abstract:

    International audienceThe aim of this work was to study the differential behavior shown by Candida antarctica lipase B during the O-Acylation and N-Acylation of monofunctional alcohols and monofunctional amines. To achieve this, 2-butanol and sec-butylamine were used as model molecules. Yields, kinetics and enantioselectivity were studied for both reactions. Although a steady-state ordered ternary complex bi-bi mechanism was obtained for the O-Acylation of 2-butanol, a ping-pong bi-bi mechanism was obtained for the N-Acylation in case of low sec-butylamine concentrations. The values of apparent kinetic parameters were calculated: the enantiomeric ratios (E) were evaluated and confirmed the preference of C. antarctica lipase B for the (R)-enantiomer, which was consistent with the literature. The enantioselectivity was calculated for the alcohol (E ≈ 3.17) and for the amine (E ≈ 1.34). Concerning the O-Acylation, the yields were found to be very similar for both enantiomers R and S. However, both initial rates and yields of the (R)-enantiomer N-Acylation were higher than those of the (S)-enantiomer. In the last part of our study, the chemoselectivity of C. antarctica lipase B was evaluated, showing that C. antarctica lipase B was a chemoselective enzyme that preferentially catalyzed the O-Acylation to the detriment of the N-Acylation (C ≈ 92, for the selective Acylation of (R)-enantiomers). These results provide new insights for the synthesis of products issued from the selective Acylation of multifunctional substrates such as amino-alcohols

Wangke Qian – One of the best experts on this subject based on the ideXlab platform.

Jianliang Xiao – One of the best experts on this subject based on the ideXlab platform.

Sung Gak Kim – One of the best experts on this subject based on the ideXlab platform.

Hong Liu – One of the best experts on this subject based on the ideXlab platform.