PMID: 2115770Jul 1, 1990Paper

The structural basis of the inhibition of human glycosidases by castanospermine analogues

The Biochemical Journal
B WinchesterG W Fleet

Abstract

A series of epimers and deoxy derivatives of castanospermine has been synthesized to investigate the contribution of the different chiral centres to the specificity and potency of inhibition of human liver glycosidases. Castanospermine inhibits all forms of alpha- and beta-D-glucosidases, but alteration to any of the five chiral centres in castanospermine markedly decreases the inhibition. 6-Epicastanospermine, which is related to D-pyranomannose in the same way as castanospermine is to D-pyranoglucose, does not inhibit lysosomal (acidic) alpha-mannosidase, but is a good inhibitor of the cytosolic or neutral alpha-mannosidase. Conversely, 1-deoxy-6-epicastanospermine inhibits acidic alpha-mannosidase strongly, but not the neutral alpha-mannosidase. An explanation of this different inhibition based on preferential recognition of different configurations of mannose by the different forms of alpha-mannosidase is postulated. All derivatives of 6-epicastanospermine also have the minimum structural feature for the inhibition of alpha-L-fucosidase, but those with a beta-anomeric substituent do not inhibit the enzyme, or do so very weakly. 1-Deoxy-6,8a-diepicastanospermine, which has four chiral centres identical with alpha-L-fucose, i...Continue Reading

Citations

May 6, 2015·Organic & Biomolecular Chemistry·Clothilde Le GuenThierry Lequeux
Jun 17, 2010·Chemical Communications : Chem Comm·Elena M Sánchez-FernándezJosé M García Fernández
May 1, 1993·Medicinal Research Reviews·R A Wiley, D H Rich
Jan 24, 2008·Chemistry : a European Journal·Laurent ChabaudKurt Schenk
Mar 20, 2010·Organic & Biomolecular Chemistry·Vincenzo ZambranoLucia Battistini
Jul 28, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Seung-Mann PaekHwayoung Yun
Jul 29, 2021·Organic & Biomolecular Chemistry·Piotr Szcześniak, Bartłomiej Furman
May 23, 2012·The Journal of Organic Chemistry·Hwayoung YunYoung-Ger Suh
Jul 29, 2017·The Journal of Organic Chemistry·Anais Vieira Da CruzSandrine Py
Nov 8, 2003·The Journal of Organic Chemistry·M Isabel García-MorenoJosé M García Fernández
May 18, 2000·The Journal of Organic Chemistry·S E Denmark, B Herbert

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