A potent new class of active-site-directed glycosidase inactivators

Tong, Michael K.; Ganem, Bruce

doi:10.1021/ja00209a062

Cited by 58 publications

(16 citation statements)

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“…Cyclophellitol-aziridine has been found to be a potent mechanism-based retaining b-exoglucosidase inhibitor. [21][22][23][24] Herein, we reveal the development of aziridine ABPs 3 and 4 and demonstrate their merits as broad-spectrum retaining bexoglucosidase probes capable of tagging the human and murine enzymes GBA, GBA2, GBA3, and LPH as well as a wide variety of non-mammalian b-exoglucosidases.…”

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confidence: 98%

Novel Activity‐Based Probes for Broad‐Spectrum Profiling of Retaining β‐Exoglucosidases In Situ and In Vivo

Kallemeijn

Witte

et al. 2012

Angewandte Chemie

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Top‐Marke: Aktivitätsbasierte Sonden vom Cyclophellitolaziridin‐Typ ermöglichen die hochempfindliche Visualisierung von β‐Glucosidasen aus Säugern (GBA1, GBA2, GBA3, and LPH) und verschiedenen anderen Lebewesen (siehe Bild). Mithilfe dieser Sonden lassen sich β‐Exoglucosidasen studieren, und Konfigurationsisomere des Cyclophellitolaziridin‐Kerns könnten aktivitätsbasierte Sonden für andere Glycosidasefamilien ergeben.

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confidence: 98%

Novel Activity‐Based Probes for Broad‐Spectrum Profiling of Retaining β‐Exoglucosidases In Situ and In Vivo

Kallemeijn

Witte

et al. 2012

Angewandte Chemie

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“…reduction of the acetylated y-lactam 19 and subsequent deblocking the trihydroxyindolizidine 24 is obtained, which is an analogue of castanospermine with L-fuco configuration. The chloride 30, which is available from 27, can be converted by intramolecular substitution and removal of the blocking groups to the bicyclic aziridine derivative (3R,4S,5R,6S)-l-azabicyclo[4.l.0]heptane-3,4,5-triol (32). First results on the inhibitory activities of all new analogues on a-L-fucosidase are presented.…”

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confidence: 99%

Monosaccharide mit Stickstoff im Ring, XXXIX. Synthese von modifizierten α‐L‐Fucosidase‐Inhibitoren, die 1,5‐Didesoxy‐1,5‐imino‐L‐fucit als Basisstruktur enthalten

et al. 1990

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Monosaccharides Containing Nitrogen in the Ring, XXXIX'). Inhibitors of a-L-FucosidaseVariation of the side chain in the 1,3-dithiane derivative 1 of D-galactose leads to a series of analogues of 1,5-dideoxy-1,5-imino-L-fucitol (deoxyfuconojirimycin) (33), which are potent inhibitors of a-L-fucosidase. Cleavage of the dithioacetal in 5 followed by reduction of the aldehyde 6 and deblocking results in 1,5-dideoxy-l,5-imino-~-galactito1 (8). The aldehyde 6 is converted by Wittig reaction to 10 and 14 via 9 and 13, which are homologues of 1,5-dideoxy-l,5-imino-~-fucitol (33). Cyclization of the Wittig product 15 yields the y-lactam 18. After

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“…The aziridine's proton accepting properties, its rigidity and its potential reactivity can all contribute to specific molecular interactions with proteins, and indeed several important natural products such as mitomycin C [16], porfiromycin [17], and carzinophilin A [18] contain the aziridine functionality. A number of saccharide derivatives containing the aziridine group have been made, mostly as intermediates [19], but also as glycosidase inhibitors [20].…”

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confidence: 99%