Synthesis of the enantiomers of XYLNAc and LYXNAc: comparison of β-N-acetylhexosaminidase inhibition by the 8 stereoisomers of 2-N-acetylamino-1,2,4-trideoxy-1,4-iminopentitols

Elizabeth V. Crabtree, R. Fernando Martínez, Shinpei Nakagawa, Isao Adachi, Terry D. Butters, Atsushi Kato, George W. J. Fleet, Andreas F. G. Glawar
2014 Organic and biomolecular chemistry  
The enantiomers of XYLNAc (2-N-acetylamino-1,2,4-trideoxy-1,4-iminoxylitol) are prepared from the enantiomers of glucuronolactone; the synthesis of the enantiomers of LYXNAc (2-N-acetylamino-1,2,4trideoxy-1,4-iminolyxitol) from an L-arabinono-δ-lactone and a D-ribono-δ-lactone is reported. A comparison is made of the inhibition of β-N-acetylhexosaminidases (HexNAcases) and α-N-acetylgalactosaminidase (α-GalNAcase) by 8 stereoisomeric 2-N-acetylamino-1,2,4-trideoxy-1,4-iminopentitols; their
more » ... ntitols; their N-benzyl derivatives are better inhibitors than the parent compounds. Both XYLNAc and LABNAc are potent inhibitors against HexNAcases. None of the compounds show any inhibition of α-GalNAcase. † Electronic supplementary information (ESI) available: NMR spectra for 20-23, 29-33, 36 and 40-46. See
doi:10.1039/c4ob00097h pmid:24802185 fatcat:6u255mguvrbujfgi7l7ewtcymm