Industrial production, application, microbial biosynthesis and degradation of furanic compound, hydroxymethylfurfural (HMF)

Abstract

Biorefinery is increasingly embraced as an environmentally friendly approach that has the potential to shift current petroleum-based chemical and material manufacture to renewable sources. Furanic compounds, particularly hydroxymethylfurfurals (HMFs) are platform chemicals, from which a variety of value-added chemicals can be derived. Their biomanufacture and biodegradation therefore will have a large impact. Here, we first review the potential industrial production of 4-HMF and 5-HMF, then we summarize the known microbial biosynthesis and biodegradation pathways of furanic compounds with emphasis on the enzymes in each pathway. We especially focus on the structure, function and catalytic mechanism of MfnB (4-(hydroxymethyl)-2-furancarboxyaldehyde-phosphate synthase) and hmfH (HMF oxidase), which catalyze the formation of phosphorylated 4-HMF and the oxidation of 5-HMF to furandicarboxylic acid (2,5-FDCA), respectively. Understanding the structure-function relationship of these enzymes will provide important insights in enzyme engineering, which eventually will find industry applications in mass-production of biobased polymers and other bulk chemicals in future.

Advances in Electrochemical Modification Strategies of 5‐Hydroxymethylfurfural

“…Recently reviewed, a wide variety of bacteria have been shown capable of HMF transformation including oxidation to high‐value products, such as DFF, 5‐hydroxymethyl‐2‐furancarboxylic acid (HFCA), FFCA, and FDCA, and HMF reduction to DHMF with the product yield and composition dependent on the utilized bacterial species [80] . Some bacterial strains investigated for HMF transformation into value‐added chemicals include Comamonas testosteroni SC1588 for the production of HFCA, [91] Methylobacterium radiotolerans G‐2 for the production of FDCA, [92] Paraburkholderia azotifigens F18 for the production of DHMF, HFCA, and FDCA, [93] Meyerozyma guilliermondii SC1103 for the production of DHMF, [94] and recombinant Escherichia coli CCZU‐K14 for the production of DHMF, [95] among others reviewed recently [80,96] . With the advances of microbial synthesis from HMF, the pairing of these studies with microbial electrochemistry offers exciting opportunities to control the selectivity and production by using an electrical current to influence the metabolisms of the bacterial cells [89] .…”

Effect of Extract and Synthesized Derivatives of Isolated Compound from Symplocos chinensis f. Pilosa Ohwi on Neuropathic Pain in Mice

“…pilosa Ohwi extract for the treatment of neuropathic pain. Because 5-HMF has a possible toxic mechanism [ 18 ], we used a Salmonella typhimurium mutagenicity based test (Ames test), which is a suitable bacterial assay to detect mutagenic potential [ 19 ].…”

“…Therefore, the aim of this study was to discover synthetic compounds based on 5-hydroxymethylfurfural (5-HMF) isolated from S. chinensis f. pilosa Ohwi extract for the treatment of neuropathic pain. Because 5-HMF has a possible toxic mechanism [18], we used a Salmonella typhimurium mutagenicity based test (Ames test), which is a suitable bacterial assay to detect mutagenic potential [19].…”

A bacterial biosynthetic pathway for methylated furan fatty acids

“…FuFAs, such as 9M5-FuFA, are one of the few classes of natural fatty acids with an oxygen atom within the hydrophobic portion of the acyl chain. Hydroxylases, lipooxygenases, or other enzymes have been proposed or shown to incorporate an oxygen atom into the furan ring of terpenoids, antimicrobials, and other compounds ( 14 , 22 , 30 – 32 ). The source of the oxygen atom in the FuFA rings is O 2 ; however, the enzyme(s) involved is unknown ( 33 , 34 ).…”