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

    Research output: Contribution to journalArticleResearchpeer-review

    122 Citations (Scopus)

    Abstract

    (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.
    Original languageEnglish
    Pages (from-to)6067-6070
    JournalOrganic Letters
    Volume8
    DOIs
    Publication statusPublished - 21 Dec 2006

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