191863-34-0Relevant academic research and scientific papers
Tight-binding inhibition of jack bean α-mannosidase by glycoimidazole clusters
Pichon, Ma?va M.,Stauffert, Fabien,Bodlenner, Anne,Compain, Philippe
, p. 5801 - 5817 (2019/06/19)
The best multivalent effects observed in glycosidase inhibition have been achieved so far with jack bean α-mannosidase (JBα-man) using iminosugar clusters based on weakly binding mismatching active-site-directed inhibiting epitopes (inhitopes) in the d-gl
Improved Access to Imidazole-phosphonic Acids: Synthesis of D-manno-Tetrahydroimidazopyridine-2-phosphonates)
Terinek, Miroslav,Vasella, Andrea
, p. 719 - 734 (2007/10/03)
The D-manno-tetrahydroimidazopyridine-2-phosphonate 11 was prepared via a high-yielding Pd(PPh3)4-catalysed diphenylphosphonylation of the manno-iodoimidazole 12, followed by transesterification to the diethyl phosphonate 14 and deal
Synthesis of C(2)-Substituted manno-Configured Tetrahydroimidazopyridines and Their Evaluation as Inhibitors of Snail β-Mannosidase
Terinek, Miroslav,Vasella, Andrea
, p. 3482 - 3509 (2007/10/03)
It was shown that retaining β-glucosidases and galactosidases of families 1-3 feature a strong interaction between C(2)OH of the substrate and the catalytic nucleophile. An analogous interaction can hardly take place for retaining β-mannosidases. A structure-activity comparison between the inhibition of the β-glucosidase from Caldocellum saccharolyticum (family 1) and β-glucosidase from sweet almonds by the gluco-imidazoles 1-6, and the inhibition of snail β-mannosidase by the corresponding manno-imidazoles 8-13 does not show any significant difference, suggesting that also the mechanisms of action of these glycosidases do not differ significantly. For this comparison, we synthesized and tested the manno-imidazoles 9-13, 28, 29, 32, 35, 40, 41, 43, 46, 47, and 50. Among these, the alkene 29 is the strongest known inhibitor of snail β-mannosidase (Ki= 6 nM, non-competitive); the aniline 35 is the strongest competitive inhibitor (Ki=8 nM).
Structure-activity relations for imidazo-pyridine-type inhibitors of β-D-glucosidases
Granier, Thierry,Panday, Narendra,Vasella, Andrea
, p. 979 - 987 (2007/10/03)
The triazole 7 and the known gluco- and manno-configurated imidazoles 10 and 11 have been prepared by annulation of the azole ring to the aldonothiolactam 14 in a Hg(OAc)2-promoted reaction with either hydrazinecarbaldehyde or aminoacetaldehyde dimethyl acetal. Depending upon the reaction conditions, the synthesis of the imidazoles yielded mostly the gluco-imidazole 19 or a mixture of the gluco/manno epimers 19/20. In contrast to the triazole 4, the isomeric triazole 7 proved a good inhibitor of retaining β-glucosidases from sweet almonds and from Caldocellum saccharolyticum. This observation and the qualitative correlation between basicity and inhibitory power of the tetrahydropyridoazoles provide further evidence for the hypothesis of the 'lateral protonation' of glycosides by (some) retaining β-glucosidases.
