Straightforward chemo-enzymatic synthesis of new aminocyclitols, analogues of valiolamine and their evaluation as glycosidase inhibitors.

Content Provider	Semantic Scholar
Author	Blidi, Lahssen El Ahbala, Mustapha Bolte, Jean Lemaire, Marielle
Copyright Year	2006
Abstract	An efficient fructose-1,6-bisphosphate aldolase mediated synthesis of new aminocyclitol analogues of valiolamine is described. The one-pot process where four stereocentres are created involves the formation of two carbon–carbon bonds. One is catalysed by the aldolase, coupling dihydroxyacetone phosphate to nitrobutyraldehydes. The other is the result of a highly stereoselective intramolecular Henry reaction occurring on the intermediate nitroketones. Depending on the configuration of the hydroxyl which is α to the nitro group, two series of configuration are accessible. The lipase resolution of the nitroalcohol ketal, precursor of the nitroaldehyde, is presented. The inhibition properties of the aminocyclitols obtained after the reduction of the nitro group are evaluated towards five commercial glycosidases
Starting Page	2684
Ending Page	2688
Page Count	5
File Format	PDF HTM / HTML
DOI	10.1016/j.tetasy.2006.09.010
Volume Number	17
Alternate Webpage(s)	https://hal.archives-ouvertes.fr/hal-00118415/document
Alternate Webpage(s)	https://doi.org/10.1016/j.tetasy.2006.09.010
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article