503-66-2Relevant academic research and scientific papers
Enzymatic synthesis of 3-hydroxypropionic acid at high productivity by using free or immobilized cells of recombinant Escherichia coli
Yu, Shanshan,Yao, Peiyuan,Li, Jianjiong,Ren, Jie,Yuan, Jing,Feng, Jinhui,Wang, Min,Wu, Qiaqing,Zhu, Dunming
, p. 37 - 42 (2016)
3-Hydroxypropionic acid (3-HP) is an important platform chemical for organic synthesis and high performance polymers. Despite a wealth of reports related to 3-HP biosynthesis in microorganisms, its industrial application still requires further research because of low titer and productivity. Herein an effective enzymatic method for the synthesis of 3-HP was achieved by using free or immobilized recombinant Escherichia coli BL21(DE3) cells harboring a nitrilase gene from environmental sample (NIT190). Under the optimal conditions (100 mmol/L Tris-HCl buffer, pH 8.0, 30 °C), the maximum substrate concentration which could be completely hydrolyzed by using free cells within 24 h was 4.5 mol/L (319.5 g/L). Furthermore, immobilization of the whole cells enhanced their substrate tolerance (up to 7.0 mol/L), stability, and reusability. The immobilized cells could be reused for up to 30 batches, and 70% of enzyme activity was retained after 74 batches in distilled water. The titer (184.7 g/L) and productivity (36.9 g/(L h)) were obtained by isolation and purification of 3-HP from the first 30 batches. These results demonstrate that the immobilized cells have potential industrial application for the synthesis of 3-HP.
Practical syntheses of the C12-C21 epothilone subunit via catalytic asymmetric reductions: Itsuno-Corey oxazaborolidine reduction and asymmetric Noyori hydrogenation
Reiff, Emily A.,Nair, Sajiv K.,Narayan Reddy,Inagaki, Jun,Henri, John T.,Greiner, Jack F.,Georg, Gunda I.
, p. 5845 - 5847 (2004)
Two practical catalytic asymmetric reductions to introduce the epothilone C15 stereocenter are described (Itsuno-Corey reduction and Noyori hydrogenation).
Efficient, chemical-catalytic approach to the production of 3-hydroxypropanoic acid by oxidation of biomass-derived levulinic acid with hydrogen peroxide
Wu, Linglin,Dutta, Saikat,Mascal, Mark
, p. 1167 - 1169 (2015)
3-Hydroxypropanoic acid (HPA), a precursor to acrylic acid, can be produced in high yield by oxidation of the biomass-derived platform chemical levulinic acid. While treatment of levulinic acid with H2O2 under acidic conditions gives predominantly succinic acid, a remarkable reversal of selectivity is observed under basic conditions, leading either directly to HPA or, under modified conditions, initially to 3-(hydroperoxy)propanoic acid, which can be quantitatively hydrogenated to HPA. Just say no to fermentation: The first selective, chemical-catalytic approach to renewable 3-hydroxypropanoic acid (HPA) has been accomplished by gentle oxidation of biomass-derived levulinic acid with hydrogen peroxide and hydrogenolysis of the resulting hydroperoxide intermediate. HPA is a green building block of major potential for the production of renewable acrylate derivatives.
Production of 3-hydroxypropionate using a novel malonyl-CoA-mediated biosynthetic pathway in genetically engineered: E. coli strain
Liang, Bo,Sun, Guannan,Wang, Zhaobao,Xiao, Jian,Yang, Jianming
, p. 6103 - 6115 (2019)
3-Hydroxypropionic acid (3-HP) is a promising platform chemical with a wide range of applications. The traditional chemical synthesis of 3-HP is well-established, but the resource limitations, high price and toxicity of the used raw materials do not meet the new sustainable development goals. Accordingly, the microbial synthesis of 3-HP by fermentation will become a promising and attractive route mainly due to its environmentally friendly production, use of renewable resources, and sustainable development. Herein, to biosynthesize 3-HP directly from malonate, a novel malonyl-CoA-mediated biosynthetic pathway was successfully developed as follows. Firstly, various transporters involved in malonate transportation was systematically investigated and screened. Secondly, to biosynthesize 3-HP, an original strategy was employed by heterologously co-expressing the mutant of malonyl-CoA reductase (MCR) from Chloroflexus aurantiacus and malonyl-CoA synthetase (MatB) from Rhodopseudomonas palustris in the Escherichia coli C43 (DE3) strain, which was screened from three different MatB enzymes. Finally, to further enhance the production of 3-HP, native transhydrogenase (PntAB) and NAD kinase (YfjB) genes were expressed to increase the NADPH supply in E. coli. The final genetically modified strain SGN78 showed a significant improvement in malonate utilization and produced 1.20 ± 0.08 g L-1 of 3-HP in the flask culture. Thus, this work demonstrates the production of 3-HP in E. coli with the shortest route for the biosynthesis of 3-HP, which involved only three steps from the substrate. Also, it opens a path for the biosynthesis of 3-HP and other malonyl-CoA-based valuable chemicals directly from malonate in E. coli.
The selective oxidation of glycerol over metal-free photocatalysts: insights into the solvent effect on catalytic efficiency and product distribution
Fan, Mingming,Haryonob, Agus,Jiang, Pingping,Leng, Yan,Yue, Chengguang,Zhang, Pingbo
, p. 3385 - 3392 (2021/06/06)
Selective oxidation of glycerol to high value-added derivatives is a promising biomass conversion pathway, but the related reaction mechanism, in particular the solvent effect, is rarely studied. In this work, O-doped g-C3N4was used as a metal-free catalyst to catalyze the selective oxidation of glycerol in different solvents. It was found that solvents can affect both catalytic efficiency and product distribution. A series of controlled experiments and theoretical calculation were applied to attest that the difference in interaction between glycerol and catalysts in different solvents is the main factor: competitive adsorption and hydrogen bond network from water inhibit the adsorption and activation of glycerol on the catalyst surface and reduce the conversion efficiency, while in acetonitrile, the stronger adsorption makes the oxidation reaction continue to yield esters. Two reaction routes in different solvents over O-doped g-C3N4are proposed for the first time, which is helpful for people to better understand the related reaction mechanism.
Method for preparing 3-hydracrylic acid through continuous hydration of acrylic acid
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Paragraph 0098, (2020/04/29)
The invention relates to a method for preparing 3-hydracrylic acid through continuous hydration of acrylic acid. The reaction is carried out in a fixed bed reactor, an acid modified molecular sieve isused as a catalyst and acrylic acid is subjected to a hydration reaction to generate 3-hydracrylic acid. The modifier adopted by the acid-modified molecular sieve is a mixture of maleic acid and maleic acid diamine or a mixture of citric acid and ammonium citrate. The modified catalyst can reduce the reaction temperature and the selectivity of byproducts, inhibit self-polymerization of acrylic acid and 3-hydracrylic acid and improve the product yield.
Expanding the repertoire of nitrilases with broad substrate specificity and high substrate tolerance for biocatalytic applications
Rayavarapu, Pratima,Shah, Shikha,Sunder, Avinash Vellore,Wangikar, Pramod P.
, p. 289 - 296 (2020/05/18)
Enzymatic conversion of nitriles to carboxylic acids by nitrilases has gained significance in the green synthesis of several pharmaceutical precursors and fine chemicals. Although nitrilases from several sources have been characterized, there exists a scope for identifying broad spectrum nitrilases exhibiting higher substrate tolerance and better thermostability to develop industrially relevant biocatalytic processes. Through genome mining, we have identified nine novel nitrilase sequences from bacteria and evaluated their activity on a broad spectrum of 23 industrially relevant nitrile substrates. Nitrilases from Zobellia galactanivorans, Achromobacter insolitus and Cupriavidus necator were highly active on varying classes of nitriles and applied as whole cell biocatalysts in lab scale processes. Z. galactanivorans nitrilase could convert 4-cyanopyridine to achieve yields of 1.79 M isonicotinic acid within 3 h via fed-batch substrate addition. The nitrilase from A. insolitus could hydrolyze 630 mM iminodiacetonitrile at a fast rate, effecting 86 % conversion to iminodiacetic acid within 1 h. The arylaliphatic nitrilase from C. necator catalysed enantioselective hydrolysis of 740 mM mandelonitrile to (R)-mandelic acid in 4 h. Significantly high product yields suggest that these enzymes would be promising additions to the suite of nitrilases for upscale biocatalytic application.
Environment-friendly and efficient synthesis method of 3-hydracrylic acid
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Paragraph 0030-0060, (2020/07/27)
The invention relates to the field of fine chemicals. The invention relates to an environment-friendly and efficient synthesis method of 3-hydracrylic acid. The method comprises the following steps: sequentially adding tetrahydrofuran, a solvent, an oxygen source and required gas into a reaction container, heating to a reaction temperature, cooling to room temperature after reaction time is reached, adding a proper amount of water, and carrying out vacuum fractionation to collect a fraction with a proper temperature, thereby obtaining the 3-hydracrylic acid product with the product yield up to58%. According to the method, environment-friendly and efficient preparation of 3-hydracrylic acid is realized under mild conditions, the used raw materials can be obtained from petrochemical engineering at low cost or by biomass catalytic conversion. The reaction conditions are very mild, the process operation is very simple, the product is very easy to separate, in addition, the cyclic utilization of an experiment solvent in the industrial production can be realized, the environment-friendly and efficient synthesis of the biomass platform compound 3-hydroxypropionic acid is realized, and meanwhile, the environment problems caused in the process flow are also avoided.
Method used for producing 3-hydroxypropionic acid
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Paragraph 0037; 0045-0047; 0050-0052; 0053-0055, (2019/12/08)
The invention belongs to the technical field of chemistry, and more specifically provides a method used for producing 3-hydroxypropionic acid. The method comprises following steps: 1, under catalyst effect, hydrogen cyanide and ethylene oxide are reacted to generated 3-hydroxypropionitrile; 2, an acid is added into the 3-hydroxypropionitrile prepared using step 1 for hydrolysis, and 3-hydroxypropionic acid and an inorganic slat are generated through reaction; 3, a reaction solution obtained in step 2 is subjected to continuous chromatography separation to obtain 3-hydroxypropionic acid and aninorganic salt solution, and the inorganic salt solution is subjected to concentration to obtain a by-product. According to the method, continuous chromatography method is adopted to process the 3-hydroxypropionitrile hydrolysis reaction solution, so that the amounts of waste water, waste gas, and waste residue can be reduced effectively, high content of the target product is obtained at high yield, and production cost is reduced.
Highly selective conversion of glyceric acid to 3-iodopropionic acid by hydriodic acid mediated hydrogenation
Li, Teng,Liu, Shengqin,Wang, Bing,Long, Jingen,Jiang, Jun,Jin, Ping,Fu, Yao,Yu, Haizhu,Yang, Weiran
supporting information, p. 4434 - 4442 (2019/08/21)
Glycerol, generated in abundance as the by-product in the process of biodiesel production and saponification, has seen attempts to convert it into value-added chemicals. However, due to the low selectivity of hydrogenolysis of the secondary hydroxyl group, valuable 1,3-substituted chemicals are difficult to obtain from glycerol by chemocatalysis. In this work, glyceric acid (GA), a renewable biomass from glycerol, was quantitatively converted to 3-iodopropionic acid (3-IPA) at 373 K in 3 h by hydroiodic acid mediated hydrogenation. As the reductant in this process, HI is oxidized to I2 and then regenerated in situ by metal catalysts and H2. The reaction pathway was proposed by intermediate identification and verified by a kinetics study and computational method. The catalytic system was shown to be stable and can be reused several times without loss in activity. As a 1,3-substituted chemical, 3-IPA is not only a potential monomer to form poly-3-hydroxypropionic acid, but also a good platform molecule to produce useful chemicals, e.g. 3-hydroxypropionic acid (3-HPA) and acrylic acid (AA), due to its highly reactive nature.
