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

摘要

2-Acetamido-1,2-dideoxy-D-galacto-nojirimycin [DGJNAc], prepared in 20% overall yield from D-glucu-ronolactone, is the first potent competitive sub-micromolar inhibitor of α-N-acetyl-galactosaminidases (K_i 0.081 μM from chicken liver, K_i 0.136 μM from Charonia lampas). DGJNAc is a good competitive-whereas the enantiomer l-DGJNAc is a very weak but non-competitive—inhibitor of β-hexosaminidases.