4437-06-3Relevant articles and documents
A plug-and-play chemobiocatalytic route for the one-pot controllable synthesis of biobased C4 chemicals from furfural
Huang, Yi-Min,Lu, Guang-Hui,Zong, Min-Hua,Cui, Wen-Jing,Li, Ning
supporting information, p. 8604 - 8610 (2021/11/16)
Chemobiocatalytic selective transformation is an attractive yet challenging task, due to the incompatibility issues between different types of catalysts. In this work, one-pot, multi-step cascades integrating biocatalysis with organo-, base- and photocatalysis in a plug-and-play fashion were constructed for the controllable synthesis of eight C4 chemicals from furfural. Furfural was converted to 5-hydroxy-2(5H)-furanone (HFO) by sequential biocatalytic oxidation and photooxygenation in phosphate buffer, in >90% yields. Ring opening and concurrent isomerization of HFO to fumaric semialdehyde (FSA) were readily realized under mild conditions by a weakly basic resin (e.g., DVB resin). The versatile intermediate FSA could be oxidized to fumaric acid (FA) using a laccase-2,2,6,6-tetramethylpiperidinyl-1-oxy (TEMPO) system, which was further upgraded to amino acids including l-aspartic acid (l-Asp) and β-alanine (β-Ala) by whole-cell catalysis. Notably, amino acids were obtained from biobased furfural in a one-pot, four-step process with yields of up to 75%, without the isolation of any intermediates. Besides, the scale-up synthesis of l-Asp was demonstrated. This work demonstrates the great potential of the combination of chemo- and biocatalysis for selective furfural valorization.
A self-organizing chemical assembly line
Salles, Airton G.,Zarra, Salvatore,Turner, Richard M.,Nitschke, Jonathan R.
supporting information, p. 19143 - 19146 (2014/01/17)
Chemical syntheses generally involve a series of discrete transformations whereby a simple set of starting materials are progressively rendered more complex. In contrast, living systems accomplish their syntheses within complex chemical mixtures, wherein the self-organization of biomolecules allows them to form assembly lines that transform simple starting materials into more complex products. Here we demonstrate the functioning of an abiological chemical system whose simple parts self-organize into a complex system capable of directing the multistep transformation of the small molecules furan, dioxygen, and nitromethane into a more complex and information-rich product. The novel use of a self-assembling container molecule to catalytically transform a high-energy intermediate is central to the system's functioning.
Catalytic oxidation of furan and hydrofuran compounds. 5. Hydroxy- and ethoxydihydrofurans and ethoxyfuran - New products from the reaction of furan with hydrogen peroxide
Poskonin,Badovskaya,Povarova
, p. 900 - 906 (2007/10/03)
It was established for the first time by chromato-mass spectrometry that 2-X-5-Y-2,5-dihydrofurans (X, Y = OH, OEt) and 2-ethoxyfuran are formed during the oxidation of furan by hydrogen peroxide in a mixture of water and ethanol in the presence of VOSO4. Stable tautomeric forms of 2-hydroxy- and 2,5-dihydroxyfurans - 2(5H)-furanone and 5-ethoxy-2(5H)-furanone respectively - were isolated from the reaction mixture. A probable scheme for the main reaction paths is proposed. 1999 Kluwer Academic/Plenum Publishers.
2,5-Dimethoxy-2,5-dihydrofuran: A convenient synthon for a novel mono-protected glyoxal; synthesis of 4-hydroxybutenolides
Fell, Stephen C. M.,Harbridge, John B.
, p. 4227 - 4228 (2007/10/02)
Ozonolysis, followed by a reductive work up of 2,5-dimethoxy-2,5-dihydrofuran generates the symmetrical bis-aldehyde (9) which reacts in situ with certain stabilized phosphoranes. Hydrolysis of the resultant alkene acetals affords 4-hydroxybutenolides (1) end (2).
