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- W2170346064 abstract "Abstract Several N‐substituted analogues of noeuromycin ((2RS,3S,4R,5R)‐2,3,4‐trihydroxy‐5‐hydroxymethylpiperidine) and isofagomine ((3R,4R,5R)‐3,4‐dihydroxy‐5‐hydroxymethylpiperidine) were synthesised. The isofagomine analogues (3RS,4RS,5RS)‐N‐(2‐phosphonoethyl)‐3,4‐dihydroxy‐5‐hydroxymethyl‐piperidine, (3SR,4SR,5RS)‐N‐(2‐phosphonoethyl)‐3,4‐dihydroxy‐5‐hydroxy‐methylpiperidine, and (3R,4R,5R)‐N‐(10‐chloro‐9‐anthracenemethyl)‐3,4‐dihydroxy‐5‐hydroxy‐methylpiperidine were synthesised by direct alkylation of the corresponding azasugar. N‐Substituted noeuromycin derivatives could not be made in this straightforward manner, but were made by modification of a synthesis intermediate. By this method (2RS,3S,4R,5R)‐N‐(4‐methoxyphenyl)‐2,3,4‐trihydroxy‐5‐hydroxymethylpiperidine and (2RS,3S,4R,5R)‐N‐nonyl‐2,3,4‐trihydroxy‐5‐hydroxymethylpiperidine were synthesised. The stability of noeuromycin was studied and was found to depend on stereochemistry and pH. The L‐fuco isomer ((2RS,3R,4R,5R)‐2,3,4‐trihydroxy‐5‐methylpiperidine) was observed to undergo a particularly facile Amadori rearrangement at neutral pH to the 3‐ketopiperidine. A noeuromycin analogue, that could not undergo the Amadori rearrangement, was synthesised. Keywords: NoeuromycinIsofagomineGlycoside metabolismGaucher's diseaseGlycosidase inhibitor1-N-Iminosugar1-AzasugarN-Alkyl Acknowledgment We thank the National Danish Research council for financial support." @default.
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- W2170346064 date "2004-12-29" @default.
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- W2170346064 title "Synthesis and Chemistry of Noeuromycin and Isofagomine Analogues" @default.
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- W2170346064 doi "https://doi.org/10.1081/car-200030070" @default.
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