918160-35-7Relevant academic research and scientific papers
Straightforward chemo-enzymatic synthesis of new aminocyclitols, analogues of valiolamine and their evaluation as glycosidase inhibitors
El Blidi, Lahssen,Ahbala, Mustapha,Bolte, Jean,Lemaire, Marielle
, p. 2684 - 2688 (2006)
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
Fructose-6-phosphate aldolases as versatile biocatalysts for nitrocyclitol syntheses
Camps Bres, Flora,Guerard-Helaine, Christine,Fernandes, Carlos,Castillo, Jose A.,Lemaire, Marielle
, p. 1175 - 1181 (2013/10/08)
Efficient and stereoselective polyhydroxylated nitrocyclitol syntheses were performed via biocatalysed aldol reactions. The key step was based on a one-pot/one-enzyme cascade reaction process where two reactions occur: aldolase-catalysed aldolisation and spontaneous intramolecular nitroaldolisation. The synthetic methodology was investigated using fructose-6-phosphate aldolase A129S for the synthesis of known nitrocyclitols. Improvements were obtained which involved less steps and increased yields. Several new nitrocyclitols were also prepared using hydroxyacetone (HA) as the donor and FSA wt. From nitrocyclitol stereochemical analyses, the intramolecular nitro-Henry reaction stereoselectivity was dependent on the donor substrate used, HA or dihydroxyacetone (DHA). Whereas DHA provided two stereoisomers, four were obtained using HA.
