Fructose-6-phosphate Aldolases as Versatile Biocatalysts for Nitrocyclitol Syntheses - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Tetrahedron: Asymmetry Année : 2013

Fructose-6-phosphate Aldolases as Versatile Biocatalysts for Nitrocyclitol Syntheses

Résumé

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.
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Dates et versions

hal-00950103 , version 1 (20-02-2014)

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  • HAL Id : hal-00950103 , version 1

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Flora Camps Bres, Christine Guérard-Hélaine, Carlos Fernandes, José A. Castillo, Marielle Lemaire. Fructose-6-phosphate Aldolases as Versatile Biocatalysts for Nitrocyclitol Syntheses. Tetrahedron: Asymmetry, 2013, 24, pp.1075-1081. ⟨hal-00950103⟩
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