Branched-chain five-membered ring aza-sugar analogues, synthesized from amino acids by an
intramolecular oxime−olefin cycloaddition reaction, the IOOC route, were found to be selective
glycosidase inhibitors. The derivative 2,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from
d-serine, was about 1 order of potency more active than its enantiomer obtained from l-serine.
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