Synthesis of 2-acetamido-1,2-dideoxy-D-galacto-nojirimycin [DGJNAc] from D-glucuronolactone: the first sub-micromolar inhibitor of α-N-acetylgalactosaminidases

2-Acetamido-1,2-dideoxy-D-galacto-nojirimycin [DGJNAc], prepared in 20% overall yield from D-glucuronolactone, is the first potent competitive sub-micromolar inhibitor of alpha-N-acetyl-galactosaminidases (K-i 0.081 mu M from chicken liver, K-i 0.136 mu M from Charonia lampas). DGJNAc is a good competitive-whereas the enantiomer L-DGJNAc is a very weak but non-competitive inhibitor of beta-hexosaminidases. (C) 2010 Published by Elsevier Ltd.