Significant Enhancement of 5-Hydroxymethylfural Productivity from <i>D</i>-Fructose with SG(SiO<sub>2</sub>) in Betaine:Glycerol–Water for Efficient Synthesis of Biobased 5-(Hydroxymethyl)furfurylamine
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...
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MDPI AG
2022-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/18/5748 |
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| author | Daozhu Xu Qi Li Jiacheng Ni Yucai He Cuiluan Ma |
| author_facet | Daozhu Xu Qi Li Jiacheng Ni Yucai He Cuiluan Ma |
| author_sort | Daozhu Xu |
| collection | DOAJ |
| description | 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 <i>D</i>-fructose in deep eutectic solvent Betaine:Glycerol–water. The introduction of Betaine:Glycerol could greatly promote the dehydration of <i>D</i>-fructose to 5-HMF and inhibit the secondary decomposition reactions of 5-HMF, compared with a single aqueous phase. <i>D</i>-Fructose (200 mM) could be catalyzed to 5-HMF (183.4 mM) at 91.7% yield by SG(SiO<sub>2</sub>) (3 wt%) after 90 min in Betaine:Glycerol (20 wt%), and at 150 °C. <i>E. coli</i> AT exhibited excellent bio-transamination activity to aminate 5-HMF into 5-HMFA at 35 °C and pH 7.5. After 24 h, <i>D</i>-fructose-derived 5-HMF (165.4 mM) was converted to 5-HMFA (155.7 mM) in 94.1% yield with <i>D</i>-Ala (<i>D</i>-Ala-to-5-HMF molar ratio 15:1) in Betaine:Glycerol (20 wt%) without removal of SG(SiO<sub>2</sub>), achieving a productivity of 0.61 g 5-HMFA/(g substrate <i>D</i>-fructose). Chemoenzymatic valorization of <i>D</i>-fructose with SG(SiO<sub>2</sub>) and <i>E. coli</i> AT was established for sustainable production of 5-HMFA, which has potential application. |
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| language | English |
| last_indexed | 2024-03-09T23:03:18Z |
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| series | Molecules |
| spelling | doaj.art-c4d2bc5a0b644adda17651e7a7c2fd5a2023-11-23T17:58:12ZengMDPI AGMolecules1420-30492022-09-012718574810.3390/molecules27185748Significant Enhancement of 5-Hydroxymethylfural Productivity from <i>D</i>-Fructose with SG(SiO<sub>2</sub>) in Betaine:Glycerol–Water for Efficient Synthesis of Biobased 5-(Hydroxymethyl)furfurylamineDaozhu Xu0Qi Li1Jiacheng Ni2Yucai He3Cuiluan Ma4School of Pharmacy, Changzhou University, Changzhou 213164, ChinaState Key Laboratory of Biocatalysis and Enzyme Engineering, Hubei University, Wuhan 430062, ChinaSchool of Pharmacy, Changzhou University, Changzhou 213164, ChinaSchool of Pharmacy, Changzhou University, Changzhou 213164, ChinaState Key Laboratory of Biocatalysis and Enzyme Engineering, Hubei University, Wuhan 430062, China5-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 <i>D</i>-fructose in deep eutectic solvent Betaine:Glycerol–water. The introduction of Betaine:Glycerol could greatly promote the dehydration of <i>D</i>-fructose to 5-HMF and inhibit the secondary decomposition reactions of 5-HMF, compared with a single aqueous phase. <i>D</i>-Fructose (200 mM) could be catalyzed to 5-HMF (183.4 mM) at 91.7% yield by SG(SiO<sub>2</sub>) (3 wt%) after 90 min in Betaine:Glycerol (20 wt%), and at 150 °C. <i>E. coli</i> AT exhibited excellent bio-transamination activity to aminate 5-HMF into 5-HMFA at 35 °C and pH 7.5. After 24 h, <i>D</i>-fructose-derived 5-HMF (165.4 mM) was converted to 5-HMFA (155.7 mM) in 94.1% yield with <i>D</i>-Ala (<i>D</i>-Ala-to-5-HMF molar ratio 15:1) in Betaine:Glycerol (20 wt%) without removal of SG(SiO<sub>2</sub>), achieving a productivity of 0.61 g 5-HMFA/(g substrate <i>D</i>-fructose). Chemoenzymatic valorization of <i>D</i>-fructose with SG(SiO<sub>2</sub>) and <i>E. coli</i> AT was established for sustainable production of 5-HMFA, which has potential application.https://www.mdpi.com/1420-3049/27/18/5748<i>D</i>-fructose5-Hydroxymethylfural5-(Hydroxymethyl)furfurylamine |
| spellingShingle | Daozhu Xu Qi Li Jiacheng Ni Yucai He Cuiluan Ma Significant Enhancement of 5-Hydroxymethylfural Productivity from <i>D</i>-Fructose with SG(SiO<sub>2</sub>) in Betaine:Glycerol–Water for Efficient Synthesis of Biobased 5-(Hydroxymethyl)furfurylamine Molecules <i>D</i>-fructose 5-Hydroxymethylfural 5-(Hydroxymethyl)furfurylamine |
| title | Significant Enhancement of 5-Hydroxymethylfural Productivity from <i>D</i>-Fructose with SG(SiO<sub>2</sub>) in Betaine:Glycerol–Water for Efficient Synthesis of Biobased 5-(Hydroxymethyl)furfurylamine |
| title_full | Significant Enhancement of 5-Hydroxymethylfural Productivity from <i>D</i>-Fructose with SG(SiO<sub>2</sub>) in Betaine:Glycerol–Water for Efficient Synthesis of Biobased 5-(Hydroxymethyl)furfurylamine |
| title_fullStr | Significant Enhancement of 5-Hydroxymethylfural Productivity from <i>D</i>-Fructose with SG(SiO<sub>2</sub>) in Betaine:Glycerol–Water for Efficient Synthesis of Biobased 5-(Hydroxymethyl)furfurylamine |
| title_full_unstemmed | Significant Enhancement of 5-Hydroxymethylfural Productivity from <i>D</i>-Fructose with SG(SiO<sub>2</sub>) in Betaine:Glycerol–Water for Efficient Synthesis of Biobased 5-(Hydroxymethyl)furfurylamine |
| title_short | Significant Enhancement of 5-Hydroxymethylfural Productivity from <i>D</i>-Fructose with SG(SiO<sub>2</sub>) in Betaine:Glycerol–Water for Efficient Synthesis of Biobased 5-(Hydroxymethyl)furfurylamine |
| title_sort | significant enhancement of 5 hydroxymethylfural productivity from i d i fructose with sg sio sub 2 sub in betaine glycerol water for efficient synthesis of biobased 5 hydroxymethyl furfurylamine |
| topic | <i>D</i>-fructose 5-Hydroxymethylfural 5-(Hydroxymethyl)furfurylamine |
| url | https://www.mdpi.com/1420-3049/27/18/5748 |
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