IOOC route to substituted chiral pyrrolidines. Potential glycosidase inhibitors

Eliezer Falb; Yosi Bechor; Abraham Nudelman; Alfred Hassner; Amnon Albeck; Hugo E. Gottlieb

doi:10.1021/jo9815094

IOOC route to substituted chiral pyrrolidines. Potential glycosidase inhibitors

Eliezer Falb, Yosi Bechor, Abraham Nudelman, Alfred Hassner, Amnon Albeck, Hugo E. Gottlieb

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

38 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	498-506
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	64
Issue number	2
DOIs	https://doi.org/10.1021/jo9815094
State	Published - 22 Jan 1999

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abstract = "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.",

author = "Eliezer Falb and Yosi Bechor and Abraham Nudelman and Alfred Hassner and Amnon Albeck and Gottlieb, {Hugo E.}",

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AU - Falb, Eliezer

AU - Bechor, Yosi

AU - Nudelman, Abraham

AU - Hassner, Alfred

AU - Albeck, Amnon

AU - Gottlieb, Hugo E.

PY - 1999/1/22

Y1 - 1999/1/22

N2 - 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.

AB - 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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IOOC route to substituted chiral pyrrolidines. Potential glycosidase inhibitors

Abstract

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