Catalysts
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2023
·Vol. 13
·期 1
·145
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IF 3.9
Yunjian Ma,Zongquan Li,Hao Zhang,Vincent Kam Wai Wong,Frank Hollmann,Yonghua Wang
Aromatic aldehydes are important aromatic compounds for the flavour and fragrance industry. In this study, a parallel cascade combining aryl alcohol oxidase fromPleurotus eryngii(PeAAOx) and unspecific peroxygenase from the basidiomyceteAgrocybe aegerita(AaeUPO) to convert aromatic primary alcohols into high-value aromatic aldehydes is proposed. Key influencing factors in the process of enzyme cascade catalysis, such as enzyme dosage, pH and temperature, were investigated. The universality ofPeAAOx coupled withAaeUPO cascade catalysis for the synthesis of aromatic aldehyde flavour compounds from aromatic primary alcohols was evaluated. In a partially optimised system (comprising 30 μMPeAAOx, 2 μMAaeUPO at pH 7 and 40 °C) up to 84% conversion of 50 mM veratryl alcohol into veratryl aldehyde was achieved in a self-sufficient aerobic reaction. Promising turnover numbers of 2800 and 21,000 forPeAAOx andAaeUPO, respectively, point towards practical applicability.Keywords:aromatic aldehydes;flavour compounds;cascade catalysis;PeAAOx;AaeUPO
研究领域:
生物化学
·
酶工程
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DOI
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APPLIED CATALYSIS B-ENVIRONMENTAL
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2018
·
IF 11.698
Xiangju Ye,Yinghao Chen,Yahui Wu,Xuemei Zhang,Xuchun Wang,Shifu Chen
In a reaction system, the simultaneously efficient utilization of photogenerated electrons and holes to realize the photocatalytic selective redox reactions of organics has been a hot topic. In this paper, the Zn 3 In 2 S 6 samples were synthesized via a simple solvothermal method with different solvents, which could make full use of photogenerated electrons and holes to achieve the photocatalytic selective transformation of aromatic alcohols to aromatic aldehydes and hydrogen evolution under mild conditions. The results show that the Zn 3 In 2 S 6 synthesized with water (Zn 3 In 2 S 6 -W) exhibits the highest photocatalytic performance among the selected samples, with which the yields of benzaldehyde and hydrogen reach up to 732 and 708.8 μmol under light irradiation (λ ≥ 380 nm) for 4 h, respectively. The molar ratios between aldehydes and hydrogen are close to 1: 1. The apparent quantum efficiency is about 6.48% for wavelength λ = 380 ± 10 nm over Zn 3 In 2 S 6 -W sample. A possible reaction mechanism for the photocatalytic selective transformation of benzyl alcohol to benzaldehyde and hydrogen evolution under light irradiation is proposed. This work highlights that a reaction system is developed to effectively make use of the photogenerated electrons and holes for selective transformation of aromatic alcohols to aromatic aldehydes and hydrogen evolution over Zn 3 In 2 S 6 photocatalysts under mild conditions.
研究领域:
化学
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材料科学
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DOI
高影响因子
JOURNAL OF ORGANIC CHEMISTRY
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2022
·
IF 4.198
Ge Liu,Yuzhen Gao,Weiping Su
An efficient protocol was proposed for the preparation of secondary alcohols in good to excellent yields via photoredox-catalyzed decarboxylative couplings between readily available arylacetic acids and a variety of less reactive (hetero)aromatic aldehydes. The formation of carbanion is the key intermediate in this reaction. Various substituted arylacetic acids and aldehydes were all compatible with this transformation under mild reaction conditions. Furthermore, the current protocol was successfully applied to the direct alcoholization of several drug acids.
研究领域:
有机化学
·
合成化学
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DOI
PubMed
高影响因子
JOURNAL OF CHEMICAL RESEARCH
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2018
·
IF 0.668
Can Jin,Feng Wang,Bin Sun,Xiaohui Zhuang
A novel method for the preparation of N-chloroaldimines from commonly available aromatic aldehydes has been developed. The reaction proceeded effectively by two steps: aldehydes were initially transformed into imines and then chloro-substitution with NaClO2 gave the N-chloroaldimines. This simple protocol allows for the preparation of a variety of aromatic N-chloroaldimines in moderate to excellent yields without the isolation of the imine intermediate. We also found that 3-nitrobenzaldehyde and 4-cyanobenzaldehyde were converted into the related benzonitrile directly under the standard conditions.
研究领域:
有机化学
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合成化学
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DOI
高影响因子
Biomass Conversion and Biorefinery
·
2021
·Vol. 12
·期 1
·87-93
·
IF 4.987
Wang Yun,Yao Qiao-Xia,He Jia-Rui,Liang Zhi-Hui,Li Xiang,Cheng Hong,Li Li-Ling
Knoevenagel condensation of acetylacetone and aromatic aldehyde catalyzed by L-proline in the choline chloride-based deep eutectic solvents was achieved. High yields are up to 96.6%. Mild reaction conditions, enhanced rates, improved yields, recyclability of deep eutectic solvents containing L-proline, and reagents’ reactivity which is different from that in standard organic solvents are the remarkable features observed in deep eutectic solvents. The deep eutectic solvents containing catalyst was recycled in four subsequent runs with no decrease in activity.
研究领域:
有机化学
·
绿色化学
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DOI
高影响因子
LANGMUIR
·
2018
·
IF 3.789
Yajie Wang,Pengyao Xing,Wei An,Mingfang Ma,Minmin Yang,Tianxiang Luan,Ruipeng Tang,Bo Wang,Aiyou Hao
Facile control over preparation of organic building blocks and self-assembled aggregations to construct the desired materials remains challenges. This article reports selective dynamic covalent bonds formation and the corresponding self-assembly behaviors by using a dipeptide, glycylglycine (GlyGly), reacting with isomeric aromatic dialdehydes o-phthalaldehyde (OPA), p-phthalaldehyde (PPA), and m-phthalaldehyde (MPA) to demonstrate diversified aggregation forms caused by structure topology variations. Under alkaline condition, the aldehyde groups of phthalaldehydes can be connected with the amino groups of GlyGly by imine bonds as the dynamic chemical bonds. Owing to the fact that formation and dissociation of the imine bonds were reversibly pH-responsive, the reactions and aggregates assembled by their products were also reversibly controlled by changing pH. Three products, including two-armed product (OPGG, in which two GlyGly molecules were connected with one OPA molecule), single-armed product (PPG, in which only one GlyGly molecule was connected with a PPA molecule), and a mixture product (MPGG and MPG), as well as their different self-assembly behaviors, were obtained from OPA/GlyGly, PPA/GlyGly, and MPA/GlyGly systems, respectively, at the same condition of pH 8.6 in 90% methanol aqueous solution. However, for OPA/GlyGly system, another different type of product with benzopyrrole structure (OPG) was obtained by nucleophilic substitution via mixing OPA and GlyGly in water, which generated organic nanoparticles. Based on the results above, we conjectured the differences in dynamic covalent bond formation and supramolecular assembly clearly were influenced by the structure topologies of phthalaldehydes (OPA, PPA, and MPA). The experimental phenomenon verified the hypothesis as well, which may guide us to realize facile construction of selective reaction products and intelligent reversibly responsive materials with diverse morphologies and functions.
研究领域:
有机化学
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材料科学
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生物化学
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DOI
PubMed
高影响因子
Biotechnology for Biofuels and Bioproducts
·
2024
·Vol. 17
·期 1
·1-12
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IF 3.3
Mo Qiwen,Yuan Jifeng
Background Vanillin represents one of the most widely used flavoring agents in the world. However, microbial synthesis of vanillin is hindered by the host native metabolism that could rapidly degrade vanillin to the byproducts. Results Here, we report that the industrial workhorse Saccharomyces cerevisiae was engineered by systematic deletion of oxidoreductases to improve the vanillin accumulation. Subsequently, we harnessed the minimal aromatic aldehyde reduction (MARE) yeast platform for de novo synthesis of vanillin from glucose. We investigated multiple coenzyme-A free pathways to improve vanillin production in yeast. The vanillin productivity in yeast was enhanced by multidimensional engineering to optimize the supply of cofactors (NADPH and S -adenosylmethionine) together with metabolic reconfiguration of yeast central metabolism. The final yeast strain with overall 24 genetic modifications produced 365.55 ± 7.42 mg l −1 vanillin in shake-flasks, which represents the best reported vanillin titer from glucose in yeast. Conclusions The success of vanillin overproduction in budding yeast showcases the great potential of synthetic biology for the creation of suitable biocatalysts to meet the requirement in industry. Our work lays a foundation for the future implementation of microbial production of aromatic aldehydes in budding yeast. Graphical Abstract
研究领域:
合成生物学
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代谢工程
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生物技术
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风味化学
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DOI
PubMed
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AUSTRALIAN JOURNAL OF CHEMISTRY
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2014
·Vol. 68
·期 6
·919-925
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IF 1.644
Jianping Wei,Fangmei Li,Junhui Xu,Xinhua Peng
New polynitrostilbenes were directly synthesised by the Knoevenagel condensation of aromatic aldehydes with nitrotoluenes. The differential scanning calorimetry results demonstrated that the introduction of an amino group and C=C double bonds could improve the thermal stability.
研究领域:
有机化学
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材料科学
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DOI
高影响因子
NEW JOURNAL OF CHEMISTRY
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2023
·Vol. 47
·期 36
·17072-17079
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IF 3.3
Hongmei Xie,Guozhi Zhu,Dawei Ye,Weiquan Cai,Junjie Zhang,Kangping Huang,Yuliang Mai,Bing Liao,Jiazhi Chen
Catechyl lignin (C-lignin) is a unique and attractive natural biopolymer used as raw material for the production of chemicals and materials due to its homogeneous linear aromatic structure. Tung nutshells, an important component of industrial solid waste, are rich in C/G-type Lignin. Herein, for the first time, we report that the catalytic oxidation strategy is effective for the conversion of Tung nutshell lignin to value-added C/G-type aromatic monomers using the commercially available CuCl2 catalyst. The reaction conditions, including solvent, temperature, and catalyst dosage, were comprehensively investigated. The optimal yield of 60.8 mg g−1 (or 12.9 wt% Klason lignin) C/G-type aromatic aldehydes and acids was obtained using the CuCl2 catalyst in the CH3CN/H2O (8/2, v/v) solvent mixture at 190 °C for 4 h. The C-type aromatic monomers were formed with an yield of 7.7 mg g−1 (or 1.6 wt%) in the initial 0.2 h and gradually decreased as the reaction progressed. The less amount of C-type lignin-derived aromatic monomers can be attributed to their lower thermal stability under oxidative conditions. The structural evolution study of lignin by GPC and HSQC NMR reveals that the C/G units are effectively depolymerized and transformed into aromatic aldehydes and acids by the CuCl2/CH3CN/H2O catalytic oxidative system.
研究领域:
化学工程
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生物质能
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有机化学
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高影响因子
Biomass Conversion and Biorefinery
·
2020
·Vol. 12
·期 12
·5555-5562
·
IF 2.602
Wang Yun,Cheng Hong,Li Xiang,Li Li-Ling,Liang Zhi-Hui,Liang Xin-Yi,Chen Xin-Yi
The catalytic promiscuity of MML, lipase from Mucor miehei, was reported to catalyze direct aldol reactions between aromatic aldehydes and cyclic ketones in water, ionic liquids, and deep eutectic solvents at 50 °C. Water can promote the catalytic activity of MML. A wide range of aromatic aldehydes reacted with cyclic ketones to provide the corresponding aldol products with high yields (up to 87.2%) and moderate to good diastereoselectivity (up to 3:97 dr).
研究领域:
生物化学
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绿色化学
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JOURNAL OF ORGANIC CHEMISTRY
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2021
·
IF 4.354
Junhua Kong,Zhi-Jiang Jiang,Jiayuan Xu,Yan Li,Hong Cao,Yanan Ding,Bencan Tang,Jia Chen,Zhanghua Gao
A practical and scalable ortho-selective deuteration of aromatic aldehydes was accomplished by Pd-catalyzed hydrogen isotope exchange with deuterium oxide as an inexpensive deuterium source. The use of tert-leucine as a transient directing group facilitates the exchange, affording a wide range of ortho-deuterated aromatic aldehydes with deuterium incorporation up to 97%. The control experiments suggest that the addition of silver trifluoroacetate resists the unexpected reduction of Pd(II), while the theoretical study indicates a rapid reversible concerted metalation–deprotonation process.
研究领域:
有机化学
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同位素化学
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PubMed
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Molecular Systems Design & Engineering
·
2023
·Vol. 8
·期 6
·767-774
·
IF 3.6
Zuobing Xiao,Chengjing Wu,Xinyu Lu,Yunwei Niu,Peiran Yu,Xiaojie Ma
Fragrance precursors are an assorted class of pro-fragrances that could realize the controlled release of aromatic compounds. Herein, nicotinoylhydrazone-based pH-triggered fragrance precursors (NTA1–NTA4) have been prepared by reacting nicotinoylhydrazine with a series of aromatic benzaldehydes bearing different electron-donating groups. The chemical structures and substituent effects have been confirmed by FT-IR, NMR, mass and ultraviolet-visible (UV-vis) spectroscopies. Controlled release studies in an acidic environment revealed that a strong electron-donating substituent accelerates the release rate, while weak electron donor groups favor the deceleration of fragrance release. Surprisingly, intramolecular hydrogen bond formation (–OH⋯NC–) has a positive impact upon the stability of the hydrazone bridge in precursor NTA4, consistent with the simulation of the molecular electrostatic potential (MEP) results. In addition, the release kinetics were also investigated and the release rate constant could be estimated with a first-order kinetic model (R2 > 0.98). Furthermore, it was demonstrated that fragrance precursors on cotton fabrics could be an efficient controlled release strategy for fragrant aldehydes after exposure to an ambient atmosphere for several days, compared to a reference sample containing the raw aroma chemicals.
研究领域:
有机化学
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材料科学
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香料技术
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高影响因子
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