Fructose-6-phosphate aldolase in organic synthesis: Preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays

José A. Castillo, Jordi Calveras, Josefina Casas, Montserrat Mitjans, M. Pilar Vinardell, Teodor Parella, Tomoyuki Inoue, Georg A. Sprenger, Jesús Joglar, Pere Clapés

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Resum

(Chemical Equation Presented) 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 β-galactosidase and α-glucosidase. © 2006 American Chemical Society.
Idioma originalAnglès
Pàgines (de-a)6067-6070
RevistaOrganic Letters
Volum8
DOIs
Estat de la publicacióPublicada - 21 de des. 2006

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