title: Fructose-6-phosphate aldolase in organic synthesis: preparation of D-fagomine, N-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.
authors.affiliation: Institute for Chemical and Environmental Research (IIQAB)-CSIC, Jordi Girona 18-26, 08034 Barcelona, Spain.
authors.forename: José A
authors.initials: JA
authors.lastname: Castillo
authors.forename: Jordi
authors.initials: J
authors.lastname: Calveras
authors.forename: Josefina
authors.initials: J
authors.lastname: Casas
authors.forename: Montserrat
authors.initials: M
authors.lastname: Mitjans
authors.forename: M Pilar
authors.initials: MP
authors.lastname: Vinardell
authors.forename: Teodor
authors.initials: T
authors.lastname: Parella
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Inoue
authors.forename: Georg A
authors.initials: GA
authors.lastname: Sprenger
authors.forename: Jesús
authors.initials: J
authors.lastname: Joglar
authors.forename: Pere
authors.initials: P
authors.lastname: Clapés
mesh_terms: D000478:Alkylation; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D005634:Fructose-Bisphosphate Aldolase / Q000737:chemistry*; D050112:Imino Pyranoses / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D050112:Imino Pyranoses; D010880:Piperidines; C105643:fagomine; D005634:Fructose-Bisphosphate Aldolase