GlcNAc-Thiazoline conformations

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 4C1 chair—as revealed by NMR, calculational, and crystallographic studies. It binds in the enzyme active site only in the pseudo-4C1 conformation, however, in which it most closely resembles the hypothetical bound substrate transition state, a 4E sofa that is approximately trigonal bipyramidal at the anomeric carbon.

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