Glycosidases transition-state analogs

Both glycosidases (61) and amylases (62) are inhibited by certain lactones, as is lysozyme, D-glucono-1,5-lactone, for example, is presumed to inhibit amylase by acting as a transition state analog because it closely approximates a half-chair conformation. However, as stated by Laszlo et al. (62), lactone inhibition cannot establish whether distortion of substrate occurs during binding, as in lysozyme, or after bond splitting to form the carbonium ion, as in proton catalysis. 

Yu, J, Choi, S Y, Moon, K D, Chung, H H, Youn, H J, Jeong, S, Park, H, Schultz, P G, A glycosidase antibody elicited against a chair-like transition state analog by in vitro immunization, Proc. Natl. Acad. Set USA, 95, 2880-2884, 1998. 

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