- Furan Carboxylic Acids Production with High Productivity by Cofactor-engineered Whole-cell Biocatalysts
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Furan carboxylic acids are useful chemicals in various industries. In this work, biocatalytic production of furan carboxylic acids was reported with high productivities by cofactor-engineered Escherichia coli cells. NADH oxidase (NOX) was introduced into E. coli harboring aldehyde dehydrogenases (ALDHs) to promote intracellular NAD+ regeneration, thus significantly enhancing ALDH-catalyzed oxidation. These engineered biocatalysts were capable of efficient aerobic oxidation of a variety of aromatic aldehydes. More importantly, they exhibited high substrate tolerance toward toxic furans. E. coli co-expressing vanillin dehydrogenase and NOX (E. coli_CtVDH1_NOX) enabled efficient oxidation of 250 mM of 5-hydroxymethylfurfural (HMF) to 5-hydroxymethyl-2-furancarboxylic acid (HMFCA), providing a productivity of 3.7 g/L h. With E. coli_CtVDH2_NOX as catalyst, up to 240 mM of furfural and 5-methoxymethylfurfural (MMF) could be smoothly oxidized. 2-Furoic acid (FCA, 227 mM) and 5-methoxymethyl-2-furancarboxylic acid (MMFCA, 287 mM) were produced in fed-batch synthesis, providing the productivities of 2.0 and 5.6 g/L h, respectively.
- Zhang, Xue-Ying,Wang, Xin,Li, Nan-Wei,Guo, Ze-Wang,Zong, Min-Hua,Li, Ning
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p. 3257 - 3264
(2020/05/25)
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- Selective synthesis of 2-furoic acid and 5-hydroxymethyl-2-furancarboxylic acid from bio-based furans by recombinant Escherichia coli cells
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Upgradation of bio-based furans into chemicals and biofuels has received great interest recently. In this work, we reported selective synthesis of furan carboxylic acids from the corresponding aldehydes by recombinant Escherichia coli cells expressing 3-succinoylsemialdehyde-pyridine dehydrogenase (SAPDH) from Comamonas testosteroni SC1588. The effects of induction and reaction conditions on whole-cell catalytic oxidation of furfural (FF) were studied. High temperature induction resulted in decreased activities of recombinant cells, likely due to improper protein folding. Nonetheless, recombinant cells induced under high temperature enable the byproduct furfuryl alcohol to be faster re-oxidized into 2-furoic acid (FCA) than those induced under low temperature. So the yield and selectivity of FCA were improved significantly by using high temperature induction, at expense of slightly longer reaction periods. The activities of recombinant cells highly depended on pH. The tolerant levels of this recombinant strain toward FF and 5-hydroxymethylfurfural (HMF) were approximately 100 mM. FCA and 5-hydroxymethyl-2-furancarboxylic acid (HMFCA) were obtained with the yields of 95–98%. FCA of up to 147 mM was produced by a fed-batch strategy, in a quantitative yield. In addition, most aromatic aldehydes tested were transformed into the target carboxylic acids by this biocatalytic method, with the yields up to 100%.
- Shi, Sai-Sai,Zhang, Xue-Ying,Zong, Min-Hua,Wang, Chuan-Fu,Li, Ning
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- Furoyl phosphonates
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A series of furoyl phosphonates bearing methyl, methoxymethyl, and diethoxyphosphorylmethyl groups in the furan ring have been synthesized via the Arbuzov reaction from the corresponding acid chlorides. NMR spectral parameters of the prepared compounds were studied. The values of coupling constants between the phosphorus nuclei and the carbon nuclei of the furan ring have been examined with relation to the location of the acylphosphoryl group in the furan ring, the nature of second substituent, and location of the latter with respect to the phosphorus-containing substituent in the furan ring. The substitution in position 4 of the furan ring of 3-furoyl phosphonates has been shown to strongly decrease the value of the coupling constant between the phosphorus nucleus and the C2 atom of the heterocycle. The interaction between the phosphorus nuclei has not been detected in the spectra of the compounds containing both diethoxyphosphorylmethyl and acylphosphonate fragments.
- Pevzner
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p. 1046 - 1053
(2016/07/06)
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- Ring Transformation of 2-Furylcarbamates to 5-Hydroxy-3-pyrrolin-2-ones
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N-Ethoxycarbonyl- and N-benzyloxycarbonyl-5-hydroxy-5-methoxyalkylpyrrolinones (6a-c) and (7a-c) together with minor products 8-10 were obtained from the photooxidation or autoxidation of corresponding 2-furylcarbamates (4a-c) and (5a-c).The catalytic hyd
- Yakushijin, Kenichi,Suzuki, Rika,Kawaguchi, Naoko,Tsuboi, Yoshinori,Furukawa, Hiroshi
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p. 2049 - 2055
(2007/10/02)
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