Synthesis of a precursor of D-fagomine by immobilized fructose-6-phosphate aldolase

Abstract

Fructose-6-phosphate aldolase (FSA) is an important enzyme for the C-C bond-forming reactions in organic synthesis. The present work is focused on the synthesis of a precursor of D-fagomine catalyzed by a mutant FSA. The biocatalyst has been immobilized onto several supports: magnetic nanoparticle clusters (mNC), cobalt-chelated agarose (Co-IDA), amino-functionalized agarose (MANA-agarose) and glyoxal-agarose, obtaining a 29.0%, 93.8%, 89.7% and 53.9% of retained activity, respectively. Glyoxal-agarose FSA derivative stood up as the best option for the synthesis of the precursor of D-fagomine due to the high reaction rate, conversion, yield and operational stability achieved. FSA immobilized in glyoxal-agarose could be reused up to 6 reaction cycles reaching a 4-fold improvement in biocatalyst yield compared to the non-immobilized enzyme.

Nutritional and bioactive characteristics of buckwheat, and its potential for developing gluten‐free products: An updated overview

“…d ‐fagomine is an iminosugar associated with buckwheat (groats, bran, leaves, and flour) as a dietary food component with biological activity and antimicrobial properties (Amezqueta et al, 2012 ). The d ‐fagomine is chemically a polyhydroxylated piperidines compound and acts as an inhibitor against the glycosidase enzyme (Masdeu et al, 2021 ). d ‐fagomine and its isomer 3,4‐di‐epi‐fagomine have been reported in buckwheat with higher concentration (43–44 mg/kg) in groats (Amezqueta et al, 2012 ).…”