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1.
J Dairy Sci ; 2024 Jul 12.
Artigo em Inglês | MEDLINE | ID: mdl-39004137

RESUMO

The lack of fat in yogurt can lead to alterations in taste and whey separation, reducing consumer acceptance. In this study, the feasibility of enhancing the quality of skim milk yogurt through a combination of transglutaminase (TG) and protein-glutaminase (PG) was investigated. The combination of TG and PG resulted in simultaneous cross-linking and deamidated of casein micelles, with PG deamidation taking priority over TG cross-linking, leading to higher solubility and lower turbidity of milk proteins compared with TG alone. When 0.06 U/mL TG and 0.03 U/mL PG were added, firmness and viscosity indexes significantly increased by 38.26 and 78.59%, respectively as compared with the control. Microscopic images revealed increased cross-linking with casein and filling of cavities by smaller sub-micelles in the combination of TG and PG treatment. Furthermore, the combination of TG and PG resolved issues of rough taste and whey separation, leading to improved overall liking. This study highlights the benefits of using both enzymes in dairy production and has important implication for future research.

2.
Org Biomol Chem ; 20(40): 7861-7885, 2022 10 19.
Artigo em Inglês | MEDLINE | ID: mdl-36185038

RESUMO

In recent years, isoquinoline-1,3(2H,4H)-dione compounds have attracted extensive attention from synthetic chemists, with the aim of finding simple, mild, green and efficient synthetic methods. In this review, we summarize the diverse range of synthetic methods employing acryloyl benzamides as key substrates to furnish isoquinoline-1,3-diones using different radical precursors, such as those containing carbon, sulphur, phosphorus, nitrogen, silicon and bromine. This will stimulate the interest of readers to engage in research in this field.


Assuntos
Bromo , Silício , Isoquinolinas/química , Benzamidas/química , Nitrogênio , Fósforo , Enxofre , Carbono
3.
Org Biomol Chem ; 20(2): 282-295, 2022 01 05.
Artigo em Inglês | MEDLINE | ID: mdl-34877952

RESUMO

Nitrogen-containing heterocycles are ubiquitous fragments of numerous natural products, pharmaceuticals, designed bioactive drug candidates and agrochemicals. During the past few decades, these compounds have received considerable attention from the synthetic chemistry community, and great efforts have been focused on the development of concise and efficient methods for the synthesis of these heterocyclic skeletons. In this review, we summarize a diverse range of synthetic methods employing ß-aminovinyl esters(ketones) as key CC-N-synthons to furnish useful bioactive heterocyclic frameworks, such as quinolines, pyridines, pyrazines, pyrroles, indoles, oxazoles, imidazoles, thiazoles, isothiazoles, pyrazoles, triazoles, and azepines, thus offering new opportunities and expanding the toolbox of synthetic chemistry reactions.

4.
J Org Chem ; 86(15): 10032-10042, 2021 08 06.
Artigo em Inglês | MEDLINE | ID: mdl-34279106

RESUMO

An effient tandem process consisting of palladium-catalyzed double-bond isomerization of long-chain olefins and subsequent intramolecular cyclization promoted by B2(OH)2 for the synthesis of aromatic oxazaheterocycles is disclosed. This strategy can also provide rapid access to pyrido[3,4-b]indoles, trans-2-olefins, and eneamides bearing various functional groups with high regio- and stereoselectivity.


Assuntos
Indóis , Paládio , Alcenos , Catálise , Ciclização , Isomerismo , Estrutura Molecular
5.
Org Biomol Chem ; 19(47): 10296-10313, 2021 12 08.
Artigo em Inglês | MEDLINE | ID: mdl-34812834

RESUMO

Phosphoramide, as an important framework of many biologically active molecules, has attracted widespread attention in recent decades. It is not only widely used in pharmaceuticals because of its excellent biological activities, but it also shows good performance in organic dyes, flame retardants and extractors. Thus, it is of great significance to develop effective and convenient methods for the synthesis of phosphoramides. In this review, the recent advancements made in the synthesis routes and applications of phosphoramides are discussed. The synthetic strategies of phosphoramides can be separated into five categories: phosphorus halides as the substrate, phosphates as the substrate, phosphorus hydrogen as the substrate, azides as the substrate and other methods. The latest examples of these methods are provided and some representative mechanisms are also described.

6.
J Org Chem ; 77(20): 9029-37, 2012 Oct 19.
Artigo em Inglês | MEDLINE | ID: mdl-22991941

RESUMO

Highly substituted benzene derivatives, including alkoxy-, iodoalkoxy-, and diiodo-substituted benzenes, can be selectively synthesized via Brønsted acid catalyzed and iodine-promoted tandem carbocyclization respectively. This reaction involved a direct process for C-C bond formation from 5,2-enyn-1-ones, and different reaction systems (Brønsted acids/electrophiles with solvents) afforded different substituted benzenes. Furthermore, the halogenated moiety and alkoxy group can be readily introduced into the benzene in a position which has not been easily obtained previously.


Assuntos
Ácidos/química , Alcenos/química , Alcinos/química , Benzeno/síntese química , Iodo/química , Cetonas/química , Benzeno/química , Catálise , Ciclização , Estrutura Molecular
7.
RSC Adv ; 12(37): 24232-24236, 2022 Aug 22.
Artigo em Inglês | MEDLINE | ID: mdl-36128530

RESUMO

A Cu(i)-catalyzed cross-coupling of primary amines with 2,2'-dibromo-1,1'-biphenyl for the synthesis of polysubstituted carbazole has been achieved. This protocol provides an efficient strategy for the synthesis of carbazole using cheap copper catalysts with diamine ligand, and it provides convenient access to a series of carbazole derivatives in moderate yields.

8.
Org Lett ; 23(7): 2399-2404, 2021 Apr 02.
Artigo em Inglês | MEDLINE | ID: mdl-33566622

RESUMO

A general procedure of 1,2-dibromination of vicinal sp3 C-H bonds of arylethanes using N-bromosuccinimide as the bromide reagent without an external initiator has been established. The modulation of the strength of the intermolecular noncovalent interactions between the solvent and arylethane ethanes, quantitatively evaluated via quantum chemical calculations, allows us to circumvent the fact that arylethane ethane cannot be dibrominated through traditional methods. The mechanism was explored by both experiments and quantum chemical calculations, revealing a radical chain with HAA process.

9.
Chem Commun (Camb) ; 57(61): 7533-7536, 2021 Jul 29.
Artigo em Inglês | MEDLINE | ID: mdl-34236369

RESUMO

A periodate lithium-oxidized difunctionalisation of aryl alkenes with thiols and electron-rich aromatics was achieved, selectively affording more than thirty carbosulphenylated products. Both experiments and quantum chemical calculations demonstrated the radical-polar nature of the processes, and that 1,2-dithioethane and thiiranium ions might play the role of intermediates.

10.
Int J Biol Macromol ; 185: 821-831, 2021 Aug 31.
Artigo em Inglês | MEDLINE | ID: mdl-34216670

RESUMO

Curdlan is a water-insoluble exopolysaccharide produced by Agrobacterium species under nitrogen starvation. The curdlan production in the ΔmdeA, ΔmetA, ΔmetH, and ΔmetZ mutants of methionine biosynthesis pathway of Agrobacterium sp. CGMCC 11546 were significantly impaired. Fermentation profiles of four mutants showed that the consumption of ammonia and sucrose was impaired. Transcriptome analysis of the ΔmetH and ΔmetZ mutants showed that numerous differentially expressed genes involved in the electron transfer chain (ETC) were significantly down-regulated, suggesting that methionine biosynthesis pathway affected the production of energy ATP during the curdlan biosynthesis. Furthermore, metabolomics analysis of the ΔmetH and ΔmetZ mutants showed that ADP and FAD were significantly accumulated, while acetyl-CoA was diminished, suggesting that the impaired curdlan production in the ΔmetH and ΔmetZ mutants might be caused by the insufficient supply of energy ATP. Finally, the addition of both dibasic sodium succinate as a substrate of FAD recycling and methionine significantly restored the curdlan production of four mutants. In conclusion, methionine biosynthesis pathway plays an important role in curdlan biosynthesis in Agrobacterium sp. CGMCC 11546, which affected the sufficient supply of energy ATP from the ETC during the curdlan biosynthesis.


Assuntos
Agrobacterium/fisiologia , Vias Biossintéticas , Metionina/metabolismo , Mutação , beta-Glucanas/metabolismo , Trifosfato de Adenosina/metabolismo , Agrobacterium/genética , Proteínas de Bactérias/genética , Fermentação , Perfilação da Expressão Gênica , Regulação Bacteriana da Expressão Gênica , Metabolômica , Nitrogênio/metabolismo
11.
Int J Biol Macromol ; 166: 61-70, 2021 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-33096177

RESUMO

Succinoglycan is an industrially important exopolysaccharide biosynthesized by bacteria. In this study, mutant strain 18052 N-11 was obtained from the wild type strain Rhizobium radiobacter ATCC 19358 by NTG mutagenesis. It has a high yield succinoglycan of 32.5 g/L cultured in a 15 L-fementer for 72 h. Succinoglycan SG-A from the wild type strain has two components, and the molecular weights were 1.55 × 107 Da and 1.26 × 106 Da, respectively. While, succinoglycan SG-N from the mutant strain was a homogeneous polysaccharide, and the molecular weight was 1.01 × 107 Da. The molecular weight of both succinoglycan was higher than those reported in literatures. DSC thermogram of SG-A showed a higher endothermic peak than that of SG-N due to the higher crystallinity of SG-A. The dynamic frequency sweep test of SG-A and SG-N showed that the elastic modulus G' and viscosity modulus G" curves intersected at 65 °C, indicating the thermally induced order-disorder conformation. The results of effect of concentrations (2.5-15%) and temperatures (25-75 °C) on apparent viscosity of SG-A and SG-N showed that the succinoglycan solutions exhibited non-Newtonian, shear-thinning behavior. Both SG-A and SG-N showed an excellent emulsification activity. The characterizations and rheological properties make SG-A and SG-N prominent candidates in food, cosmetics, pharmaceutical and petroleum industries.


Assuntos
Agrobacterium tumefaciens/metabolismo , Polissacarídeos Bacterianos/química , Viscosidade , Agrobacterium tumefaciens/genética , Configuração de Carboidratos , Módulo de Elasticidade , Temperatura Alta , Mutação , Polissacarídeos Bacterianos/biossíntese , Reologia
12.
J Org Chem ; 75(4): 1305-8, 2010 Feb 19.
Artigo em Inglês | MEDLINE | ID: mdl-20088585

RESUMO

A domino reaction via palladium-catalyzed Sonogashira coupling of benzimidoyl chlorides with 1,6-enynes and then cyclization to form quinoline derivatives has been developed. The reaction conditions and the scope of the process are examined, and a plausible mechanism is proposed. The procedure is simple, rapid, and general, and the substrates are readily available.


Assuntos
Alcinos/química , Benzamidas/química , Paládio/química , Quinolinas/síntese química , Catálise , Ciclização , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Quinolinas/química , Relação Estrutura-Atividade
13.
Chem Commun (Camb) ; 56(100): 15627-15630, 2020 Dec 21.
Artigo em Inglês | MEDLINE | ID: mdl-33245739

RESUMO

A formal hydroxylation/cyclization of cyclopropanemethanols with DMSO is described, which involves isomerization and cyclization under Tf2O catalysis. This reaction undergoes ring-opening of the cyclopropane moiety to generate homoallylic alcohols, which react with DMSO to produce 3-benzylidenetetrahydrofurans. With various substituted groups on cyclopropanemethanols the reactions proceed smoothly and the desired 3-benzylidenetetrahydrofurans are obtained in moderate to good yields.

14.
Int J Biol Macromol ; 165(Pt A): 222-230, 2020 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-32987068

RESUMO

Curdlan is a neutral linear exopolysaccharide produced by Agrobacterium spp. under nitrogen-limiting conditions. In this study, we explored the role of glnA in curdlan biosynthesis in Agrobacterium sp. CGMCC 11546. The curdlan production of the ΔglnA strain was impaired, decreasing by 93% compared with that of the wild-type strain after 96 h fermentation. Analysis of fermentation profiles revealed that cell growth and utilization of carbon and nitrogen sources were impaired in the ΔglnA strain. Transcriptome analysis indicated that various of genes involved in curdlan biosynthesis were downregulated after 24 h fermentation in the ΔglnA strain, particularly genes involved in heme synthesis and the electron transport chain, which are essential for energy generation. Metabolomics analysis revealed flavin adenine dinucleotide (FAD) and adenosine diphosphate (ADP) accumulation in the ΔglnA strain, suggesting insufficient energy supply. Furthermore, glnA overexpression led to an 18% increase in the curdlan yield of the ΔglnA mutant compared with that of the wild-type strain after 96 h fermentation. Taken together, the findings demonstrate that glnA plays a vital role in curdlan biosynthesis by supplying ATP via regulating the expression of genes involved in heme synthesis and the electron transport chain.


Assuntos
Agrobacterium/metabolismo , Proteínas de Bactérias/metabolismo , Glutamato-Amônia Ligase/metabolismo , beta-Glucanas/metabolismo , Agrobacterium/genética , Proteínas de Bactérias/genética , Glutamato-Amônia Ligase/genética , Mutação
15.
J Org Chem ; 74(7): 2893-6, 2009 Apr 03.
Artigo em Inglês | MEDLINE | ID: mdl-19271738

RESUMO

Ag-catalyzed cyclization of 2-alkynyl benzyl azides offers a novel and efficient method for the synthesis of substituted isoquinoline. The reaction proceeds smoothly in moderate to good yields and tolerates considerable functional groups. The reaction conditions and the scope of the process are examined, and a plausible mechanism is proposed.


Assuntos
Azidas/química , Benzeno/química , Isoquinolinas/síntese química , Prata/química , Alquilação , Catálise , Ciclização , Elétrons , Isoquinolinas/química , Estrutura Molecular
16.
Org Lett ; 21(19): 7956-7960, 2019 Oct 04.
Artigo em Inglês | MEDLINE | ID: mdl-31513418

RESUMO

The palladium-N-heterocyclic carbene (NHC)-catalyzed allylic alkylation of various pronucleophiles with alkynes has been accomplished under mild conditions. The protocol exhibits broad functional group compatibility and high atom economy. Moreover, the catalytic process avoids the use of external oxidants and acid as additives.

17.
Org Lett ; 20(16): 5048-5052, 2018 08 17.
Artigo em Inglês | MEDLINE | ID: mdl-30067037

RESUMO

A Cu-catalyzed method for the synthesis of 3,3'-bipyrroles from homopropargylic amines through tandem aerobic oxidative cyclization involving the formation of C-C bond has been developed. The features of this reaction are a small number of Cu catalysis and simple starting substrates. Moreover, this procedure exhibits good functional group tolerance and a series of 3,3'-bipyrroles derivatives are obtained in moderate to good yields.

18.
Chem Commun (Camb) ; 51(30): 6598-600, 2015 Apr 18.
Artigo em Inglês | MEDLINE | ID: mdl-25775109

RESUMO

A novel and efficient I2-catalyzed oxidative tandem cyclization of simple vinyl azides and benzylamines has been developed for the synthesis of substituted imidazoles. In this reaction, various substituted groups on vinyl azides and benzylamines proceed smoothly and the desired imidazoles are obtained in moderate to good yields.


Assuntos
Azidas/química , Benzilaminas/química , Imidazóis/química , Imidazóis/síntese química , Iodo/química , Catálise , Técnicas de Química Sintética
19.
Chem Commun (Camb) ; 49(14): 1410-2, 2013 Feb 18.
Artigo em Inglês | MEDLINE | ID: mdl-23310929

RESUMO

A new and efficient catalytic approach to the synthesis of 3-acylindoles under Pd-Cu-cocatalyzed oxidative conditions is demonstrated. tert-Butyl hydroperoxide (TBHP) acts not only as the oxidant, but also as an oxygen source in the approach. The process allows quick and atom-economical assembly of 3-acylindoles from readily available starting materials and tolerates a broad range of functional groups.


Assuntos
Cobre/química , Indóis/química , Paládio/química , Catálise , Ciclização , Indóis/síntese química , Acoplamento Oxidativo
20.
Org Lett ; 11(15): 3206-9, 2009 Aug 06.
Artigo em Inglês | MEDLINE | ID: mdl-19572605

RESUMO

A mild and direct process for C-C bond formation from propargylic alcohols and olefin has been developed in the presence of a silver catalyst. In this reaction, trace amounts of water were necessary and allene alcohols 2 and 1,3-dienes 3 were obtained selectively.


Assuntos
Alcenos/química , Alcinos/química , Carbono/química , Propanóis/química , Antimônio/química , Catálise , Cristalografia por Raios X , Ciclização , Estrutura Molecular , Prata/química
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