Bioorganic And Medicinal Chemistry
The title compound, a powerful inhibitor of retaining N-acetylhexosaminidases, can move freely among three pyranose solution conformations of similar energy-two twist boats and the (4)C(1) chair-as revealed by NMR, calculational, and crystallographic studies. It binds in the enzyme active site only in the pseudo-(4)C(1) conformation, however, in which it most closely resembles the hypothetical bound substrate transition state, a (4)E sofa that is approximately trigonal bipyramidal at the anomeric carbon. (C) 2009 Elsevier Ltd. All rights reserved.
S. Knapp, D. Fash, M. Abdo, T. J. Emge, and Paul R. Rablen.
Bioorganic And Medicinal Chemistry.