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IOOC Route to Substituted Chiral Pyrrolidines. Potential Glycosidase Inhibitors

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journal contribution
posted on 31.12.1998, 00:00 by Eliezer Falb, Yosi Bechor, Abraham Nudelman, Alfred Hassner, Amnon Albeck, Hugo E. Gottlieb
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.