Piperidine Azasugars Displaying Competitive α-Rhamnosidase Inhibition and their Kinetic Mechanism
2011
Cho, J.K., Gyeongsang National University, Jinju, Republic of Korea | Rengasamy, Rajesh, Gyeongsang National University, Jinju, Republic of Korea | Curtis-Long, Marcus John, Brandeis University, South Street Waltham, MA, USA | Kim, J.H., National Academy of Agricultural Science, RDA, Suwon, Republic of Korea | Lee, J.W., Gyeongsang National University, Jinju, Republic of Korea | Park, K.H., Gyeongsang National University, Jinju, Republic of Korea
Azasugars derived from L-alanine and L-serine were screened for inhibitory activity against α-rhamnosidase. The enantiomers of 1,6-dideoxynojirimycin (ent-1,6-dDNJ) (1) and (2S,3R)-2-(hydroxymethyl)piperidin-3-ol (5) showed highly specific and potent inhibition against α-rhamnosidase with K∧i values of 4.2 and 16.6 μM, respectively. Structure of the best inhibitor features the same stereochemical configuration as L-rhamnose at C2, C3, and C4 centers. In kinetic studies, both compounds exhibited competitive inhibition behavior. Compound 1 manifested simple reversible slow-binding inhibition with the following kinetic parameters: k₃= 1.17 nM-¹ min-¹, k₄= 5.96×10-³ min-¹, and K∧i∨app=5.1 mM.
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