Lipase-catalyzed kinetic resolution of a series of esters having a sulfoxide group as the stereogenic centre
作者： Stig G. Allenmark , A.Christina Andersson
DOI: 10.1016/S0957-4166(00)80104-4
关键词: Alkyl 、 Sulfoxide 、 Kinetic resolution 、 Benzoates 、 Substrate (chemistry) 、 Stereocenter 、 Candida rugosa 、 Lipase 、 Stereochemistry 、 Chemistry
摘要: Abstract A series of methyl 2-(alkylsulfinyl)benzoates (alkyl = C 1 , n -C 4 8 12 and 16 ) was investigated with respect to substrate behaviour enantioselectivity in a lipase ( Candida rugosa )-catalyzed hydrolytic reaction. Although three bonds separate the stereogenic centre ester carbonyl group, very high values > 100) could be obtained. It found that enzyme consistently showed strong kinetic preference for (−)-(S)-enantiomer.
elsevier.com
sci-hub.se 参考文章(13)
Philip E. Sonnet, Mary Welch Baillargeon, Methyl-branched octanoic acids as substrates for lipase-catalyzed reactions. Lipids. ,vol. 26, pp. 295- 300 ,(1991) , 10.1007/BF02537140
Stig Allenmark, Ann Ohlsson, Enantioselectivity of lipase‐catalyzed hydrolysis of some 2‐chloroethyl 2‐arylpropanoates studied by chiral reversed‐phase liquid chromatography Chirality. ,vol. 4, pp. 98- 102 ,(1992) , 10.1002/CHIR.530040206
Waldemar Adam, Michael Schwarm, How mechanistically equivalent are singlet oxygen and triazolinedione Journal of Organic Chemistry. ,vol. 53, pp. 3129- 3130 ,(1988) , 10.1021/JO00248A047
Jacek Bojarski, Joachim Oxelbark, Christina Andersson, Stig Allenmark, Enantioselective lipase-catalyzed ester hydrolysis: effects on rates and enantioselectivity from a variation of the ester structure. Chirality. ,vol. 5, pp. 154- 158 ,(1993) , 10.1002/CHIR.530050309
Zhi Wei Guo, Charles J. Sih, Enantioselective inhibition: strategy for improving the enantioselectivity of biocatalytic systems Journal of the American Chemical Society. ,vol. 111, pp. 6836- 6841 ,(1989) , 10.1021/JA00199A053
Shih Hsiung Wu, Zhi Wei Guo, Charles J. Sih, Enhancing the enantioselectivity of Candida lipase-catalyzed ester hydrolysis via noncovalent enzyme modification Journal of the American Chemical Society. ,vol. 112, pp. 1990- 1995 ,(1990) , 10.1021/JA00161A052
Michael J. S. Dewar, Eve G. Zoebisch, Eamonn F. Healy, James J. P. Stewart, Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model Journal of the American Chemical Society. ,vol. 107, pp. 3902- 3909 ,(1985) , 10.1021/JA00299A024
Romas J. Kazlauskas, Alexandra N. E. Weissfloch, Aviva T. Rappaport, Louis A. Cuccia, A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa Journal of Organic Chemistry. ,vol. 56, pp. 2656- 2665 ,(1991) , 10.1021/JO00008A016
Erland Holmberg, Erik Dahlen, TorbjÖRn Norin, Karl Hult, Enhanced Resolution of a Secondary Alcohol by Hydrolysis of a Bichiral Ester Catalyzed by Lipase from Candida cylindracea Biocatalysis. ,vol. 4, pp. 305- 312 ,(1991) , 10.3109/10242429109000694
Koji Sode, Tomoyasu Sugiyama, Takehiro Yamamoto, Masamitsu Tomiyama, Isao Karube, Restoration of Escherichia coli hyd B Mutant Hydrogenase by Cultivation in Media Containing Various Metals Biocatalysis. ,vol. 4, pp. 211- 217 ,(1990) , 10.3109/10242429008992092