The Protein Journal

, Volume 30, Issue 3, pp 220–227 | Cite as

Stereoselective Inhibition of Cholesterol Esterase by Enantiomers of exo- and endo-2-Norbornyl-Nn-butylcarbamates

  • Ming-Cheng Lin
  • Shyh-Jei Yeh
  • I-Ru Chen
  • Gialih Lin


Four stereoisomers of 2-norbornyl-Nn-butylcarbamates are characterized as the pseudo substrate inhibitors of cholesterol esterase. Cholesterol esterase shows enantioselective inhibition for enantiomers of exo- and endo-2-norbornyl-Nn-butylcarbamates. For the inhibitions by (R)-(+)- and (S)-(−)-exo-2-norbornyl-Nn-butylcarbamates, the R-enantiomer is 6.8 times more potent than the S-enantiomer. For the inhibitions by (R)-(+)- and (S)-(−)-endo-2-norbornyl-Nn-butyl-carbamates, the S-enantiomer is 4.6 times more potent than the R-enantiomer. The enzyme-inhibitor complex models have been proposed to explain these different enantioselectivities.


Cholesterol esterase Inhibitors Carbamates Enantiomers 



Acyl chain binding site


Cholesterol esterase


Low-density lipoprotein


p-nitrophenyl butyrate


Triton-X 100



We thank the National Science Council of Taiwan for financial support.


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Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Ming-Cheng Lin
    • 1
  • Shyh-Jei Yeh
    • 2
  • I-Ru Chen
    • 2
  • Gialih Lin
    • 2
  1. 1.Department of Internal Medicine, Chung Shan Medical University Hospital, School of MedicineChung-Shan Medical UniversityTaichungTaiwan
  2. 2.Department of ChemistryNational Chung-Hsing UniversityTaichungTaiwan

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