Fructose-6-phosphate Aldolase in Organic Synthesis: Preparation of <scp>d</scp>-Fagomine, <i>N</i>-Alkylated Derivatives, and Preliminary Biological Assays

Abstract

[Structure: see text] D-fructose-6-phosphate aldolase (FSA) mediates a novel straightforward two-step chemo-enzymatic synthesis of D-fagomine and some of its N-alkylated derivatives in 51% isolated yield and 99% de. The key step is the FSA-catalyzed aldol addition of simple dihydroxyacetone (DHA) to N-Cbz-3-aminopropanal. The use of FSA greatly simplifies the enzymatic procedures that used dihydroxyacetonephosphate or DHA/esters. Some N-alkyl derivatives synthesized elicited antifungal and antibacterial activity as well as enhanced inhibitory activity, and selectivity against beta-galactosidase and alpha-glucosidase.