Significant Enhancement of 5-Hydroxymethylfural Productivity from ID/I-Fructose with SGfurfurylamine

• Published in: Molecules (Basel, Switzerland) Switzerland), 2022-09, Vol.27 (18)
• Main Authors: Xu, Daozhu, Li, Qi, Ni, Jiacheng, He, Yucai, Ma, Cuiluan
• Format: Article
• Language: English
• Subjects: Fructose; Glycerin; Glycerol; Organic compounds; Production processes
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules27185748

5-Hydroxymethyl-2-furfurylamine (5-HMFA) as an important 5-HMF derivative has been widely utilized in the manufacture of diuretics, antihypertensive drugs, preservatives and curing agents. In this work, an efficient chemoenzymatic route was constructed for producing 5-(hydroxymethyl)furfurylamine (5-HMFA) from biobased D-fructose in deep eutectic solvent Betaine:Glycerol–water. The introduction of Betaine:Glycerol could greatly promote the dehydration of D-fructose to 5-HMF and inhibit the secondary decomposition reactions of 5-HMF, compared with a single aqueous phase. D-Fructose (200 mM) could be catalyzed to 5-HMF (183.4 mM) at 91.7% yield by SG(SiO[sub.2] ) (3 wt%) after 90 min in Betaine:Glycerol (20 wt%), and at 150 °C. E. coli AT exhibited excellent bio-transamination activity to aminate 5-HMF into 5-HMFA at 35 °C and pH 7.5. After 24 h, D-fructose-derived 5-HMF (165.4 mM) was converted to 5-HMFA (155.7 mM) in 94.1% yield with D-Ala (D-Ala-to-5-HMF molar ratio 15:1) in Betaine:Glycerol (20 wt%) without removal of SG(SiO[sub.2] ), achieving a productivity of 0.61 g 5-HMFA/(g substrate D-fructose). Chemoenzymatic valorization of D-fructose with SG(SiO[sub.2] ) and E. coli AT was established for sustainable production of 5-HMFA, which has potential application.