- IOOC route to substituted chiral pyrrolidines. Potential glycosidase inhibitors
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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.
- Falb, Eliezer,Bechor, Yosi,Nudelman, Abraham,Hassner, Alfred,Albeck, Amnon,Gottlieb, Hugo E.
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p. 498 - 506
(2007/10/03)
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- Utilization of L-serine in an oxime olefin cycloaddition route to a functionalized asymmetric pyrrolidine, a selective α-glucosidase inhibitor
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A new route for asymmetric aza-sugar analogs starting with L-serine and utilizing an intramolecular oxime olefin cycloaddition has been successfully developed. A member of this family of branched chain sugar amino di(hydroxymethyl) pyrrolidines (1 and 2) exhibits selective inhibition of α-glucosidase, while no inhibition of β-glucosidase was detected.
- Hassner, Alfred,Falb, Eliezer,Nudelman, Abraham,Albeck, Amnon,Gottlieb, Hugo E.
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p. 2397 - 2400
(2007/10/02)
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