Fructose-6-phosphate aldolase in organic synthesis: preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays.
[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.
Castillo
José A
JA
Institute for Chemical and Environmental Research (IIQAB)-CSIC, Jordi Girona 18-26, 08034 Barcelona, Spain.
Calveras
Jordi
J
Casas
Josefina
J
Mitjans
Montserrat
M
Vinardell
M Pilar
MP
Parella
Teodor
T
Inoue
Tomoyuki
T
Sprenger
Georg A
GA
Joglar
Jesús
J
Clapés
Pere
P
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*
D000900:Anti-Bacterial Agents; D050112:Imino Pyranoses; D010880:Piperidines; C105643:fagomine; D005634:Fructose-Bisphosphate Aldolase