Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 438234
Title The Development of an Aza-C-Glycoside Library Based on a Tandem Staudinger/Aza-Wittig/Ugi Three-Component Reaction
Author(s) Wennekes, T.; Bonger, K.M.; Vogel, K.; Berg, S.A. van den; Strijland, A.; Donker-Koopman, W.E.; Aerts, J.; Marel, A. van der; Overkleeft, H.S.
Source European Journal of Organic Chemistry 2012 (2012)32. - ISSN 1434-193X - p. 6420 - 6454.
DOI http://dx.doi.org/10.1002/ejoc.201200923
Department(s) Laboratory for Organic Chemistry
VLAG
Publication type Refereed Article in a scientific journal
Publication year 2012
Keyword(s) ugi 4-component condensation - gaucher-disease - multicomponent reactions - nonlysosomal glucosylceramidase - functionalized pyrrolidines - pharmacological chaperones - n-butyldeoxynojirimycin - combinatorial libraries - bicyclic scaffolds - storage disorders
Abstract We report the tandem Staudinger/aza-Wittig/Ugi three-component reaction mediated synthesis of a 64-member compound library of aza-C-glycosides. The library is composed of four pyrrolidine and three piperidine scaffolds, onto which a number of functional groups is grafted to form seven sublibraries. Variation in the library is achieved by transformation of two pentoses and a hexose into the corresponding 4-azidopentanal and 5-azidohexanal derivatives as precursors for the Staudinger/aza-Wittig process. Further variation is achieved by using different isocyanides as well as protective- and functional-group manipulations on the fully protected Ugi-3CR intermediates. Preliminary biological evaluation of the compound library revealed several low micromolar inhibitors of human acid glucosylceramidase
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