Chemoselective Lipase-Catalyzed Synthesis of Amido Derivatives from 5-Hydroxymethylfurfurylamine ...

• Main Authors: Pintor, Antía, Lavandera, Iván, Volkov, Alexey, Gotor-Fernández, Vicente
• Format: Dataset
• Language: English
• Published: Zenodo 2023
• Subjects: acylation; chemoselective process; enzyme immobilization; 5-hydroxymethylfurfurylamine; lipases; Antarc*; Antarctica
• Online Access: https://dx.doi.org/10.5281/zenodo.10320137; https://zenodo.org/doi/10.5281/zenodo.10320137

The acylations of furfurylamine and 5-hydroxymethylfurfurylamine (HMFA) have been studied finding immobilized Candida antarctica lipase B (CALB) as an ideal biocatalyst. CALB was used immobilized on two different supports (Novozyme 435 and EziG-CALB), with the polymer-coated controlled porosity glass carrier material from EnginZyme being an excellent carrier to yield an active and stable enzymatic preparation for the acylation of the primary amine group. The amount of the acyl donor in the reaction was a key factor to achieve the mono- and chemoselective N-protection of HMFA with large excess of ethyl acetate leading to the formation of the N,O-diacetylated product. Thus, a series of 16 nonactivated esters were used to selectively modify the amine group of HMFA, obtaining 9 hydroxy amides under mild reaction conditions and with quantitative yields through chromatography-free transformations. The influence of substrate concentration was studied, resulting in complete conversions in all cases after 22 h ...