944329-24-2Relevant academic research and scientific papers
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
Crabtree, Elizabeth V.,Martinez, R. Fernando,Nakagawa, Shinpei,Adachi, Isao,Butters, Terry D.,Kato, Atsushi,Fleet, George W. J.,Glawar, Andreas F. G.
, p. 3932 - 3943 (2014/06/09)
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-1,2,4-trideoxy-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 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. This journal is the Partner Organisations 2014.
Enantiomeric 2-acetamido-1,4-dideoxy-1,4-iminoribitols as potential pyrrolidine hexosaminidase inhibitors
Rountree, J.S. Shane,Butters, Terry D.,Dwek, Raymond A.,Fleet, George W.J.
experimental part, p. 126 - 133 (2012/02/02)
2-Acetamido-1,4-imino-1,2,4-trideoxy-D-ribitol (DRBNAc) and the enantiomeric LRBNAc were prepared as potential hexosaminidase inhibitors from L- and D-lyxonolactone, respectively. Neither N-benzyl-DRBNAc nor N-benzyl-LRBNAc showed any inhibition of α- or
Synthesis of 2-amido, 2-amino, and 2-azido derivatives of the nitrogen analogue of the naturally occurring glycosidase inhibitor salacinol and their inhibitory activities against O-GlcNAcase and NagZ enzymes
Choubdar, Niloufar,Bhat, Ramakrishna G.,Stubbs, Keith A.,Yuzwa, Scott,Pinto, B. Mario
, p. 1766 - 1777 (2008/12/21)
Seven 2-substituted derivatives of the nitrogen analogue of salacinol, a naturally occurring glycosidase inhibitor, were synthesized for structure-activity studies with hexosaminidase enzymes. The target zwitterionic compounds were synthesized by means of
Efficient synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases
Rountree, J.S.Shane,Butters, Terry D.,Wormald, Mark R.,Dwek, Raymond A.,Asano, Naoki,Ikeda, Kyoko,Evinson, Emma L.,Nash, Robert J.,Fleet, George W.J.
, p. 4287 - 4291 (2008/02/12)
The synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc proceeded in an overall yield of 25%; the enantiomer, 2-acetamido-1,4-imino-1,2,4-trideoxy-d-arabinitol DABNAc, was prepared from l-lyxonolactone. LABNAc and N-
