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One-pot three-component Mannich reaction catalyzed by sucrose char sulfonic acid

Qiong XU, Zhigao YANG, Dulin YIN, Jihui WANG

《化学科学与工程前沿（英文）》 2009年 第3卷 第2期   页码 201-205 doi: 10.1007/s11705-009-0052-5

摘要： Sucrose char sulfonic acid efficiently catalyzed the one-pot three-component Mannich reaction of ketones, aromatic aldehydes and amines in ethanol to afford the corresponding -amino carbonyl compounds in good to excellent yields. A series of heteroaromatic -amino carbonyl compounds can be obtained when using 2-acetylpyrazine as substrate. This reaction can be performed under mild reaction conditions with clean reaction profiles and a simple workup procedure.

关键词： One–pot synthesis     b-amino ketone     char sulfonic acid     2-acetylpyrazine     catalysis    

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Synthesis and anticancer activity of (+)-nopinone-based 2-amino-3-cyanopyridines

Shengliang LIAO,Shibin SHANG,Minggui SHEN,Xiaoping RAO,Hongyan SI,Jie SONG,Zhanqian SONG

《农业科学与工程前沿（英文）》 2015年 第2卷 第4期   页码 335-340 doi: 10.15302/J-FASE-2015079

摘要： Twelve (+)-nopinone-based 2-amino-3-cyanopyridines 4a–l were synthesized from (–)-β-pinene. The structures of these compounds were characterized by FT-IR, H NMR, and ESI-MS. All the compounds were tested for their anticancer activity against lung cancer cell line A549, gastric cancer cell line MKN45 and breast cancer cell line MCF7 by MTT method, respectively. The results showed that compounds 4f, 4j and 4k had promising anticancer activity against these cancer cell lines, in particular, compound 4f exhibited broad-spectrum and highly efficient anticancer activity against cell lines A549, MKN45 and MCF7 with IC of 23.78, 67.61 and 53.87 µmol·L , respectively. The preliminary analysis of the structure activity relationship implied that the Br or Cl substituted group of the benzene ring in these derivatives significantly contributed to the anticancer activity.

关键词： b-pinene     nopinone     synthesis     2-amino-3-cyanopyridine     anticancer    

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Valorisation of protein waste: An enzymatic approach to make commodity chemicals? ?

Madura B. A. Kumar, Yuan Gao, Wei Shen, Lizhong He

《化学科学与工程前沿（英文）》 2015年 第9卷 第3期   页码 295-307 doi: 10.1007/s11705-015-1532-4

摘要： Protein-rich waste is an abundantly available resource that is currently used mainly as animal feed and fertilizers. Valorisation of protein waste to higher value products, particularly commodity chemicals such as precursors for polymers, has attracted significant research efforts. Enzyme-based approaches, being environmentally-friendly compared to their chemical counterparts, promise sustainable processes for conversion of protein waste to valuable chemicals. This review provides a general overview on valorisation of protein waste and then further summarises the use of enzymes in different stages of the valorisation process—protein extraction and hydrolysis, separation of individual amino acids and their ultimate conversion into chemicals. Case studies of enzymatic conversion are presented for different amino acids including glutamic acid, lysine, phenylalanine, tyrosine, arginine and aspartic acid. The review compares the different enzyme reactors and operation modes for amino acid conversion. The emerging opportunities and challenges in the field are discussed: engineering powerful enzymes and integrating innovative processes for industrial application at a low cost.

关键词： amino acids     protein waste     reactor     conversion     commodity chemicals     enzymes    

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Catalytic conversion of biomass-derived compounds to various amino acids: status and perspectives

《化学科学与工程前沿（英文）》 2023年 第17卷 第7期   页码 817-829 doi: 10.1007/s11705-022-2254-z

摘要： Amino acids are important nitrogen-containing chemicals that have a variety of applications. Currently, fermentation is the widely employed method to produce amino acids; however, the products are mostly limited to natural amino acids in the L-configuration. Catalytic synthesis is an alternative approach for the synthesis of amino acids with different types and configurations, where the use of renewable biomass-based feedstocks is highly attractive. To date, several lignocellulose and triacylglycerol-derived intermediates, typically α-keto acids and α-hydroxyl acids, have been transformed into amino acids via the amination reaction in the presence of additional nitrogen sources (i.e., NH3·H2O). Making full use of inherent nitrogen in biomass (i.e., chitin and protein) to produce amino acids avoids the use of extra nitrogen sources and meets the requirements of green chemistry, which is attracting increasing attention. In this review, we summarize different chemical-catalytic systems for the transformation of biomass to amino acids. An outlook on the challenges and opportunities for more effective production of amino acids from biomass by catalytic methods is provided.

关键词： biomass     amino acids     chitin     nitrogen-containing compounds     lignocellulose    

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4-Amino-1,8-naphthalimide based fluorescent photoinduced electron transfer (PET) pH sensors as liposomal

Bright, Emma B. Veale, Adam F. Henwood, D. Clive Williams, Thorfinnur Gunnlaugsson

《化学科学与工程前沿（英文）》 2020年 第14卷 第1期   页码 61-75 doi: 10.1007/s11705-019-1862-8

摘要： Four new fluorescent sensors ( - ) based on the 4-amino-1,8-naphthalimide fluorophores ( ) have been synthesized based on the classical fluorophore-spacer-receptor model. These four compounds all gave rise to emission bands centred at 535 nm, which were found to be highly pH dependent, the emission being ‘switched on’ in acidic media, while being quenched due to PET from the amino moieties to the excited state of the at more alkaline pH. The luminescent pH dependence for these probes was found to be highly dependent on the substitution on the imide site, as well as the polyamine chain attached to the position 4-amino moiety. In the case of sensor the presence of the 4-amino-aniline dominated the pH dependent quenching. Nevertheless, at higher pH, PET quenching was also found to occur from the polyamine site. Hence, is better described as a receptor -spacer -fluorophore-spacer -receptor system, where the dominant PET process is due to (normally less favourable) ‘directional’ PET quenching from the 4-amino-aniline unit to the site. Similar trends and pH fluorescence dependences were also seen for and . These compounds were also tested for their imaging potential and toxicity against HeLa cells (using DRAQ5 as nuclear stain which does now show pH dependent changes in acidic and neutral pH) and the results demonstrated that these compounds have reduced cellular viability at moderately high concentrations (with IC values between ca. 8‒30 µmol∙L ), but were found to be suitable for intracellular pH determination at 1 µmol∙L concentrations, where no real toxicity was observed. This allowed us to employ these as lysosomal probes at sub-toxic concentrations, where the based emission was found to be pH depended, mirroring that seen in aqueous solution for , with the main fluorescence changes occurring within acidic to neutral pH.

关键词： sensors     pH     photoinduced electron transfer     cellular imaging     confocal microscopy    

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Insights into the changes of amino acids, microbial community, and enzymatic activities related with

《环境科学与工程前沿（英文）》 2023年 第17卷 第3期 doi: 10.1007/s11783-023-1635-y

摘要：

● The highest seed germination index was achieved at 0.3 g/g total solids of food waste.

关键词： Composting     Food waste     Amino acids     Microbial community     Enzymatic activity     Nutrient quality    

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Asymmetric transfer hydrogenation of prochiral ketone catalyzed over Fe-CS/SBA-15 catalyst

XUE Ping, WU Tao

《化学科学与工程前沿（英文）》 2007年 第1卷 第3期   页码 251-255 doi: 10.1007/s11705-007-0045-1

摘要： A heterogeneous chiral catalyst Fe(III)-CS (chitosan) complex/mesoporous molecular sieve SBA-15 (Santa Barbara Amorphous) was prepared. The asymmetric transfer hydrogenations of prochiral acetophenone and 4-methyl-2-pentanone to corresponding chiral alcohols were carried out on Fe-CS/SBA-15 at atmosphere pressure using 2-propanol as hydrogen donor. Effects of Fe content in catalyst, reaction temperature, reaction time and promoter KOH concentration on the conversion of substrates and enantioselectivity were investigated. Fe-CS/SBA-15 with 2.2% mass fraction Fe exhibits considerable enantioselectivity and catalytic activity for the asymmetric transfer hydrogenations of aromatic ketone and aliphatic ketone. Under optimal reaction conditions: KOH concentration 0.03 mol/L, reaction temperature 70ºC and reaction time 4 h, enantiomer excess (ee) of ()-1-phenylethanol and conversion of acetophenone can reach 87.4% and 27.7%, respectively. Under the above KOH concentration and reaction temperature and reaction time of 8 h, the ee of ()-4-methyl-2-pentanol and conversion 4-methyl-2-pentanone amounted to 50.2% and 25.5%, respectively.

关键词： asymmetric transfer     enantioselectivity     Fe-CS/SBA-15     aliphatic     aromatic    

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Immobilization of penicillin G acylase onto amino-modified silica hydrogel

Weibing Dong, Huining HE, Junbo Gong, Victor C. YANG,

《化学科学与工程前沿（英文）》 2010年 第4卷 第1期   页码 87-90 doi: 10.1007/s11705-009-0298-y

摘要： Amino-modified silica hydrogel (N-MSHG) was prepared by a simple sol-gel processing via the co-condensation of commercial silica sol with 3-aminopropyltrie-oxysilane. Penicillin G acylase (PGA), a model enzyme, was covalently immobilized onto the N-MSHG and then was used for the enzymatic synthesis of amoxicillin. The samples were characterized by Nitrogen sorption analysis, FT-IR and thermal gravimetric analysis (TGA). The results showed that the amino-modified gel was a mesoporous material with an average pore size of 12.64±0.17nm. The immobilization process was efficient and the immobilized enzyme showed high catalytic efficiency. The yield of the synthesis of amoxicillin in aqueous media was 38% for 2.5h. This sol-gel preparation is simple and shows prominent potential value in industrial processing.

关键词： gravimetric     amino-modified     efficient     Amino-modified     amoxicillin    

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Insulin resistance and the metabolism of branched-chain amino acids

null

《医学前沿（英文）》 2013年 第7卷 第1期   页码 53-59 doi: 10.1007/s11684-013-0255-5

摘要：

Insulin resistance (IR) is a key pathological feature of metabolic syndrome and subsequently causes serious health problems with an increased risk of several common metabolic disorders. IR related metabolic disturbance is not restricted to carbohydrates but impacts global metabolic network. Branched-chain amino acids (BCAAs), namely valine, leucine and isoleucine, are among the nine essential amino acids, accounting for 35% of the essential amino acids in muscle proteins and 40% of the preformed amino acids required by mammals. The BCAAs are particularly responsive to the inhibitory insulin action on amino acid release by skeletal muscle and their metabolism is profoundly altered in insulin resistant conditions and/or insulin deficiency. Although increased circulating BCAA concentration in insulin resistant conditions has been noted for many years and BCAAs have been reported to be involved in the regulation of glucose homeostasis and body weight, it is only recently that BCAAs are found to be closely associated with IR. This review will focus on the recent findings on BCAAs from both epidemic and mechanistic studies.

关键词： branched-chain amino acids     leucine     isoleucine     valine     insulin resistance    

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Anaerobic digestion of sludge by different pretreatments: Changes of amino acids and microbial community

《环境科学与工程前沿（英文）》 2022年 第16卷 第2期 doi: 10.1007/s11783-021-1458-7

摘要：

•Tryptophan protein, and aromatic protein I/II were the key identified proteins.

关键词： Sludge pretreatments     Dissolved organic nitrogen     Proteins     Amino acids     Structural equation model     Metagenomic sequencing analysis.    

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Sodium butyrate activates HMGCS2 to promote ketone body production through SIRT5-mediated desuccinylation

《医学前沿（英文）》 2023年 第17卷 第2期   页码 339-351 doi: 10.1007/s11684-022-0943-0

摘要： Ketone bodies have beneficial metabolic activities, and the induction of plasma ketone bodies is a health promotion strategy. Dietary supplementation of sodium butyrate (SB) is an effective approach in the induction of plasma ketone bodies. However, the cellular and molecular mechanisms are unknown. In this study, SB was found to enhance the catalytic activity of 3-hydroxy-3-methylglutaryl-CoA synthase 2 (HMGCS2), a rate-limiting enzyme in ketogenesis, to promote ketone body production in hepatocytes. SB administrated by gavage or intraperitoneal injection significantly induced blood β-hydroxybutyrate (BHB) in mice. BHB production was induced in the primary hepatocytes by SB. Protein succinylation was altered by SB in the liver tissues with down-regulation in 58 proteins and up-regulation in 26 proteins in the proteomics analysis. However, the alteration was mostly observed in mitochondrial proteins with 41% down- and 65% up-regulation, respectively. Succinylation status of HMGCS2 protein was altered by a reduction at two sites (K221 and K358) without a change in the protein level. The SB effect was significantly reduced by a SIRT5 inhibitor and in Sirt5-KO mice. The data suggests that SB activated HMGCS2 through SIRT5-mediated desuccinylation for ketone body production by the liver. The effect was not associated with an elevation in NAD+/NADH ratio according to our metabolomics analysis. The data provide a novel molecular mechanism for SB activity in the induction of ketone body production.

关键词： sodium butyrate     succinylation     HMGCS2     ketogenesis     SIRT5    

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Continuous amino-functionalized University of Oslo 66 membranes as efficacious polysulfide barriers for

《化学科学与工程前沿（英文）》 2023年 第17卷 第2期   页码 194-205 doi: 10.1007/s11705-022-2206-7

摘要： The shuttle effect of soluble polysulfides is a serious problem impeding the development of lithium−sulfur batteries. Herein, continuous amino-functionalized University of Oslo 66 membranes supported on carbon nanotube films are proposed as ion-permselective interlayers that overcome these issues and show outstanding suppression of the polysulfide shuttle effect. The proposed membrane material has appropriately sized pores, and can act as ionic sieves and serve as barriers to polysulfides transport while allowing the passage of lithium ions during electrochemical cycles, thereby validly preventing the shuttling of polysulfides. Moreover, a fast catalytic conversion of polysulfides is also achieved with the as-developed interlayer. Therefore, lithium−sulfur batteries with this interlayer show a desirable initial capacity of 999.21 mAh·g–1 at 1 C and a durable cyclic stability with a decay rate of only 0.04% per cycle over 300 cycles. Moreover, a high area capacity of 4.82 mAh·cm–2 is also obtained even under increased sulfur loading (5.12 mg·cm–2) and a lean-electrolyte condition (E/S = 4.8 μL·mg–1).

关键词： lithium−sulfur batteries     amino-functionalized University of Oslo 66 membrane     polysulfide     interlayer    

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Solvent-resistant porous membranes using poly(ether−ether ketone): preparation and application

《化学科学与工程前沿（英文）》 2023年 第17卷 第10期   页码 1536-1559 doi: 10.1007/s11705-022-2221-8

摘要： Poly(ether−ether ketone) (PEEK) is a linear aromatic macromolecule, which can form semi-crystalline aggregative status, allowing PEEK materials to have strong environment tolerance and excellent physicochemical properties. PEEK materials have become a promising alternative to fabricate particular membranes used in extreme conditions. In the past few decades, many researches and evolutions have emerged in membrane fabrication with PEEK materials and its applications for treating organic solvents and their mixtures; however, there are little systematic and comprehensive literature to summarize fabrication approaches, compile applications, and elaborate PEEK property-structure relationship. In this review, the main approaches to fabricate PEEK-based membranes are illustrated concretely, including conventional thermal-induced and non-solvent-induced phase separation, and novel chemical-induced crystallization; the representative applications in ultrafiltration, nanofiltration and membrane contactor containing organic solvents are demonstrated systematically. Meanwhile, the mechanism to tune PEEK solubility in solvents, which can be achieved by altering monomers in synthesis processes or changing membrane preparation routes, is deeply analyzed. Moreover, the existing problems and the future prospects are also discussed. This review provides positive guidance for designing and fabricating membranes using PEEK and its derivative materials for task-specific applications in harsh conditions.

关键词： PEEK     phase inversion     solvent-resistant membrane     nanofiltration     membrane contactor    

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Sulfonated poly(ether ether ketone)/zirconium tricarboxybutylphosphonate composite proton-exchange membranes

GAO Qijun, HUANG Mianyan, WANG Yuxin, CAI Yuquan, XU Li

《化学科学与工程前沿（英文）》 2008年 第2卷 第1期   页码 95-101 doi: 10.1007/s11705-008-0012-5

摘要： Sulfonated poly(ether ether ketone) (SPEEK) is a very promising alternative membrane material for direct methanol fuel cells. However, with a fairly high degree of sulfonation (DS), SPEEK membranes can swell excessively and even dissolve at high temperature. This restricts membranes from working above a high tolerable temperature to get high proton conductivity. To deal with this contradictory situation, insolvable zirconium tricarboxybutylphosphonate (Zr(PBTC)) powder was employed to make a composite with SPEEK polymer in an attempt to improve temperature tolerance of the membranes. SPEEK/Zr(PBTC) composite membranes were obtained by casting a homogeneous mixture of Zr(PBTC) and SPEEK in N,N-dimethylacetamide on a glass plate and then evaporating the solvent at 60°C. Many characteristics were investigated, including thermal stability, liquid uptake, methanol permeability and proton conductivity. Results showed significant improvement not only in temperature tolerance, but also in methanol resistance of the SPEEK/Zr(PBTC) composite membranes. The membranes containing 30 wt-% ∼ 40 wt-% of Zr(PBTC) had their methanol permeability around 10 cm·s at room temperature to 80°C, which was one order of magnitude lower than that of Nafion115. High proton conductivity of the composite membranes, however, could also be achieved from higher temperature applied. At 100% relative humidity, above 90°C the conductivity of the composite membrane containing 40 wt-% of Zr(PBTC) exceeded that of the Nafion115 membrane and even reached a high value of 0.36 S·cm at 160°C. Improved applicable temperature and high conductivity of the composite membrane indicated its promising application in DMFC operations at high temperature.

关键词： homogeneous mixture     PBTC     zirconium tricarboxybutylphosphonate     Nafion115     DMFC    

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Improvement in the synthesis of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(Z)-methoxyiminoacetic acid 2-benzothiazolyl

GAO Shihao, SUN Chenghui, ZHAO Xinqi, GAO Changquan

《化学科学与工程前沿（英文）》 2008年 第2卷 第1期   页码 80-84 doi: 10.1007/s11705-008-0017-0

摘要： 2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(Z)-methoxyiminoacetic acid 2-benzothiazolyl thioester(III), an important intermediate of the fourth generation cephalosporins, was efficiently synthesized by reacting 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(Z)-methoxyiminoacetic acid (I) with 2,2′-dibenzothiazole disulfide (II) in the presence of triphenylphosphine. Effects of reaction time, temperature, solvents, catalysts and feeding molar ratio on the yield and quality of products were investigated, and an improved procedure suitable for industrial production was established. Using 1,2-dichloroethane as solvent, triphenylphosphine as reducer, and triethylamine as catalyst, (I) : (II) : (triphenylphosphine) = 1.0 : 1.0 : 1.0, the product was obtained at room temperature in 98.1% yield. The purity of the product without further purification is 98.7% determined by HPLC method. This procedure could be a suitable alternative to the traditional processes because of its easy handling, high yield and low cost.

关键词： 5-Amino-1     2     4-thiadiazol-3-yl     1     2-dichloroethane     important intermediate     2-benzothiazolyl thioester     temperature    

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标题 作者 时间 类型 操作

One-pot three-component Mannich reaction catalyzed by sucrose char sulfonic acid

Qiong XU, Zhigao YANG, Dulin YIN, Jihui WANG

期刊论文

Synthesis and anticancer activity of (+)-nopinone-based 2-amino-3-cyanopyridines

Shengliang LIAO,Shibin SHANG,Minggui SHEN,Xiaoping RAO,Hongyan SI,Jie SONG,Zhanqian SONG

期刊论文

Valorisation of protein waste: An enzymatic approach to make commodity chemicals? ?

Madura B. A. Kumar, Yuan Gao, Wei Shen, Lizhong He

期刊论文

Catalytic conversion of biomass-derived compounds to various amino acids: status and perspectives

期刊论文

4-Amino-1,8-naphthalimide based fluorescent photoinduced electron transfer (PET) pH sensors as liposomal

Bright, Emma B. Veale, Adam F. Henwood, D. Clive Williams, Thorfinnur Gunnlaugsson

期刊论文

Insights into the changes of amino acids, microbial community, and enzymatic activities related with

期刊论文

Asymmetric transfer hydrogenation of prochiral ketone catalyzed over Fe-CS/SBA-15 catalyst

XUE Ping, WU Tao

期刊论文

Immobilization of penicillin G acylase onto amino-modified silica hydrogel

Weibing Dong, Huining HE, Junbo Gong, Victor C. YANG,

期刊论文

Insulin resistance and the metabolism of branched-chain amino acids

null

期刊论文

Anaerobic digestion of sludge by different pretreatments: Changes of amino acids and microbial community

期刊论文

Sodium butyrate activates HMGCS2 to promote ketone body production through SIRT5-mediated desuccinylation

期刊论文

Continuous amino-functionalized University of Oslo 66 membranes as efficacious polysulfide barriers for

期刊论文

Solvent-resistant porous membranes using poly(ether−ether ketone): preparation and application

期刊论文

Sulfonated poly(ether ether ketone)/zirconium tricarboxybutylphosphonate composite proton-exchange membranes

GAO Qijun, HUANG Mianyan, WANG Yuxin, CAI Yuquan, XU Li

期刊论文

Improvement in the synthesis of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(Z)-methoxyiminoacetic acid 2-benzothiazolyl

GAO Shihao, SUN Chenghui, ZHAO Xinqi, GAO Changquan

期刊论文