FOOD CHEMISTRY
·
2020
·
IF 6.306
Yuting Li,Haiping Qi,Meiqi Fan,Zixing Zhu,Shijie Zhan,Lin Li,Bing Li,Xia Zhang,Xianglong Zhao,Jingjing Ma,Lifeng Wang
The reaction efficiency of o -benzoquinones with amines (L-lysine, Nα-acetyl-L-lysine, glycine, L-methionine and L-arginine), thiols (L-cysteine and Nα-acetyl-L-cysteine) and protein (bovine serum albumin) were determined at pH 5.0, 7.0 and 8.0 and scan rate of 10, 50 and 100 mV/s by cyclic voltammetry. Nucleophiles containing multiple nucleophilic groups and nucleophilic group possessing low pKa value would enhance the reactivity of nucleophiles towards o -benzoquinones. The reactivity of different o -benzoquinones with L-lysine/L-cysteine followed the order: protocatechuic acid quinone ≈ catechol quinone > 4-methylbenzoquinone ≈ caffeic acid quinone > rosmarinic acid quinone > chlorogenic acid quinone. The reactivity of quinones would be decreased by the steric hindrance of substituents on quinone ring, and it would also be weakened by enhancing electron cloud density of quinone ring. Adducts generated by the interaction of 4-methylbenzoquinone with amines and thiols were tentatively identified as amine-quinone adduct and thiol-phenol adduct respectively by UPLC-QTOF-MS/MS and cyclic voltammetry.
研究领域:
生物化学
·
电化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
TETRAHEDRON
·
2014
·
IF 2.817
Jing Yang,Shaohuan Sun,Biao Zhang,Juan Zhang,Yanlong Gu
2-Alkoxy-3,4-dihydropyrans were proved to be a class of powerful modular substrates to construct polyheterocycles by reacting with NH 2 -containing dinucleophiles, such as anthranilamide , 2-aminobenzenethiol, 1-(2-aminophenyl)pyrrole, and 2-( o -aminophenyl)indole in the presence of LiBr·H 2 O. A three-component reaction of isatoic anhydride , 2-alkoxy-3,4-dihydropyran and amine was also developed as well.
研究领域:
有机化学
·
药物化学
✓ 已验证
产品关联
DOI
高影响因子
CHEMICAL ENGINEERING JOURNAL
·
2022
·
IF 16.744
Chen Zhong,He Zhao,Hongbin Cao,Ching-Hua Huang
Halobenzoquinones (HBQs), a metabolism of pentachlorophenol, arouse increasing concern for their high toxicity. This paper systematically studied the influences of 31 extracellular nucleophiles on the removal of dichlorobenzoquinones (DCBQs). The results showed that at pH 6.0–8.0, the transformation of DCBQs followed a pattern of pseudo first-order reaction. With the presence of different thiol compound (ratio 1:1), the apparent rate constant of 25DCBQ and 26DCBQ was between 0.028 and 0.204 min −1 and 0.061–0.156 min −1 , respectively, which was 6.6–48.3 times faster than direct hydrolysis and 1.9–23.4 times of that with histidine, a typical amino acid. This was attributed to the different transformation pathways of DCBQs with thiol or amino groups. According to the MS spectrum and transition state theory, thiol compounds was stably incorporated into DCBQs via Michael addition or substitution, which also decreased the oxidative stress of DCBQs by 35.5–86.4% and cytotoxicity of hydrolyzed DCBQ by 44.9–100%, respectively. Conversely, amino acids promoted the hydrolysis of DCBQs by forming unstable AA-DCBQ intermediates that can be further hydrolyzed to OH-DCBQs, leading to an increased selectivity of OH-DCBQs, and increased the oxidative stress of 25DCBQs by 0.2–31.2% and cytotoxicity of hydrolyzed 25DCBQ by 42.0–52.7%. Such difference was inherently related to the nucleophilicity of different atoms. Moreover, it was revealed that the maximum condensed local nucleophilicity index of nucleophiles ( N k, max ) can joint describe the relationship among nucleophilic structures, transformation pathways and toxicity of DCBQs. This paper provided a comprehensive perspective on the fast removal and detoxification of HBQs in extracellular environment.
研究领域:
环境化学
·
毒理学
·
有机化学
✓ 已验证
DOI
高影响因子
Polymer Chemistry
·
2021
·Vol. 12
·期 30
·4347-4358
·
IF 5.582
Junnan He,Nan Zheng,Ming Li,YuBin Zheng,Wangze Song
Multicomponent polymerization has emerged as a promising strategy to develop functional polymers with versatile structures. In this work, a Cu-catalyzed four-component polymerization was developed using diynes, sulfonyl azides, nucleophiles, and a variety of electrophiles including alkyl glyoxylates, nitroalkenes, and Morita–Baylis–Hillman adducts to successfully synthesize a library of α-functionalized poly(N-sulfonylimidates)s with a wide substrate scope and high molecular weights (up to 20 000 g mol−1) in high yields (up to 86%). Such α-functionalized poly(N-sulfonylimidates)s could be further post-modified or utilized for the design of multi-functional and biodegradable polymers.
研究领域:
高分子化学
·
材料科学
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）