Fructose 1,6-Diphosphate Aldolase Catalyzed Stereoselective Synthesis of C-Alkyl and N-Containing Sugars: Thermodynamically Controlled C-C Bond Formations.

Article abstract of DOI:10.1021/jo00253a004

Fructose 1,6-diphosphate aldolase catalyzed aldol condensations have been used in syntheses of several new N-containing and C-alkyl sugars on 4-20 mmol scales.The enzyme is highly specific for dihydroxyacetone phosphate as donor but accepts a number of achiral and chiral aldehydes (both D and L isomers) as acceptors.Due to the reversible nature of the aldol reaction, a thermodynamically controlled approach was employed for the syntheses in which racemic aldehydes were used as substrates and thermodynamically more stable products were preferentially produced.