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ACS Omega · 2025 · IF 4.3

Analysis of O-Glycans by Oxidative Release Combined with 3-Nitrophenylhydrazine Derivatization

Zhenghu Min,Xingdan Wang,Xiaoqiu Yang,Qiwei Zhang,Qi Zheng

Glycosylation profiling is an effective methodology for achieving a comprehensive understanding of glycoproteins and their alterations in a multitude of pathological conditions. However, in comparison to N-glycosylation, O-glycosylation presents significant challenges in terms of both qualitative and quantitative mass spectrometric analyses. A recently developed oxidative release protocol enables the selective formation of O-glycans containing a carboxyl group derived from the amino acid residue. In this study, 3-nitrophenylhydrazine was used to derivatize the common carboxyl group in a mild hydrophilic solution. Derivatization resulted in the generation of a series of report ions for serine, threonine, sialic acid, and O-acetylated sialic acid residues, thereby facilitating the identification of O-glycans and their attached amino acid residues, as well as the determination of the number of O-acetyl groups. A total of 65 O-glycans can be identified from bovine mucin. Furthermore, the analytical strategy revealed that O-acetylated N-acetylneuraminic acid (Neu5Ac)-containing O-glycans from horse serum exhibited distinctive fragmentation patterns in comparison to those from bovine mucin. Additionally, the presence of deaminoneuraminic acid (KDN)-containing O-glycans was successfully confirmed in fish intestinal tissue. These findings suggest that this method provides an economical and potentially valuable tool for large-scale O-glycosylation studies in complex biological samples.

研究领域: 生物化学 · 蛋白质组学 · 分析化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2024 · IF 5.7

Optimized Synthesis and Antioxidant Activity of Anthocyanins Delphinidin-3-O-glucoside and Petunidin-3-O-glucoside

Guangkai Wu,Zihan Zhao,Jun Hu,Yue Li,Jianxia Sun,Weibin Bai

The chemical synthesis of anthocyanins, especially delphinidin-3-O-glucoside and petunidin-3-O-glucoside, is preferable due to the challenges associated with their extraction and purification. However, the reported methods for the synthesis are scarce and intricate. Our research focused on exploring a one-step ester-to-ketone process and optimizing the ring formation reaction, simplifying and improving the overall synthesis strategy. Through these attempts, we were able to achieve higher production yields of delphinidin-3-O-glucoside and petunidin-3-O-glucoside. According to the results of DPPH, ABTS, and FRAP, the antioxidant activity of anthocyanins was increased with the number of B ring hydroxyl substituent. Additionally, both delphinidin-3-O-glucoside and petunidin-3-O-glucoside exhibited no cytotoxicity effects, highlighting their potential for safe application in various fields.

CAS / MDL: 75-05-8 75-16-1
研究领域: 化学 · 药学 · 生物化学 · 食品科学
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ANALYTICAL CHEMISTRY · 2024 · IF 6.7

MOTAI: A Novel Method for the Study of O-GalNAcylation and Complex O-Glycosylation in Cancer

Shuang Yue,Xiaotong Wang,Lei Wang,Jiajia Li,Yufeng Zhou,Yan Chen,Zeyang Zhou,Xiaodong Yang,Xiaofeng Shi,Song Gao,Zhongmin Wen,Xiaojun Zhu,Yan Wang,Shuang Yang

The Tn antigen, an immature truncated O-glycosylation, is a promising biomarker for cancer detection and diagnosis. However, reliable methods for analyzing O-GalNAcylation and complex O-glycosylation are lacking. Here, we develop a novel method, MOTAI, for the sequential analysis of O-glycosylation using different O-glycoproteases. MOTAI conjugates glycopeptides on a solid support and releases different types of O-glycosylation through sequential enzymatic digestion by O-glycoproteases, including OpeRATOR and IMPa. Because OpeRATOR has less activity on O-GalNAcylation, MOTAI enriches O-GalNAcylation for subsequent analysis. We demonstrate the effectiveness of MOTAI by analyzing fetuin O-glycosylation and Jurkat cell lines. We then apply MOTAI to analyze colorectal cancer and benign colorectal polyps. We identify 32 Tn/sTn-glycoproteins and 43 T/sT-glycoproteins that are significantly increased in tumor tissues. Gene Ontology analysis reveals that most of these proteins are ECM proteins involved in the adhesion process of the intercellular matrix. Additionally, the protein disulfide isomerase CRELD2 has a significant difference in Tn expression, and the abnormally glycosylated T345 and S349 O-glycosylation sites in cancer group samples may promote the secretion of CRELD2 and ultimately tumorigenesis through ECM reshaping. In summary, MOTAI provides a powerful new tool for the in-depth analysis of O-GalNAcylation and complex O-glycosylation. It also reveals the upregulation of Tn/sTn-glycoproteins in colorectal cancer, which may provide new insights into cancer biology and biomarker discovery.

研究领域: 癌症生物学 · 糖生物学 · 生物化学 · 分子生物学 · 临床诊断
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ACS Catalysis · 2016 · IF 9.307

Photocatalytic Oxidation–Hydrogenolysis of Lignin β-O-4 Models via a Dual Light Wavelength Switching Strategy

Nengchao Luo,Min Wang,Hongji Li,Jian Zhang,Huifang Liu,Feng Wang

One of the challenges of depolymerizing lignin to valuable aromatics lies in the selective cleavage of the abundant C–O bonds of β-O-4 linkages. Herein we report a photocatalytic oxidation–hydrogenolysis tandem method for cleaving C–O bonds of β-O-4 alcohols. The Pd/ZnIn2S4 catalyst is used in the aerobic oxidation of α-C–OH of β-O-4 alcohols to α-C═O with 455 nm light, and then a TiO2–NaOAc system is employed for cleaving C–O bonds neighboring the α-C═O bonds through a hydrogenolysis reaction by switching to 365 nm light. Interestingly, the oxidation–hydrogenolysis tandem reaction can be conducted in one pot to offer ketones and phenols (up to 90% selectivity) via a dual light wavelength switching (DLWS) strategy. EPR and metal loading experiments elucidate that Ti3+ in TiO2 is formed in situ and is responsible for the photocatalytic hydrogenolysis through electron transfer from Ti3+ to the β-O-4 ketones.

研究领域: 化学工程 · 材料科学 · 环境科学
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ACS Applied Materials & Interfaces · 2020 · IF 8.758

Multi-Encapsulation Combination of O/W/O Emulsions with Polyurea Microcapsules for Controlled Release and Safe Application of Dimethyl Disulfide

Lirui Ren,Bin Huang,Wensheng Fang,Daqi Zhang,Hongyan Cheng,Zhaoxin Song,Dongdong Yan,Yuan Li,Qiuxia Wang,Zhiqiang Zhou,Aocheng Cao

Dimethyl disulfide (DMDS), a promising alternative fumigant, has been highly desirable for excellent management of soil pests and diseases. However, high volatility and moderate toxicity of this sulfide limit its application. To address these issues, a novel controlled release formulation of DMDS was proposed employing multiple emulsions and polyurea microcapsules (DMDS@MEs-MCs). The successful combination of the two technologies was revealed by confocal laser scanning microscopy, scanning electron microscopy, thermogravimetric analysis, and Fourier transform infrared. According to the multiple encapsulation structure, the encapsulation efficiency decreased by only 3.13% after thermal storage, compared with a 15.21% decrease of microcapsules made with only a monolayer film. DMDS@MEs-MCs could effectively control the release of active ingredient, which increased applicator and environmental safety during application. Moreover, it could be facilely used by spraying and drip irrigation instead of a special fumigation device. The innovative formulation exhibited better control efficacy on soil pathogens (Fusarium spp. and Phytophthora spp.) and root-knot nematodes (Meloidogyne spp.) than DMDS technical concentration (DMDS TC). In addition, it did not inhibit seed germination after 10 days when the plastic film was removed from the fumigated soil. This method appears to be of broad interest for the development of safe and handy fumigant application.

研究领域: 农业科学 · 化学工程 · 植物病理学 · 环境科学
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BIOSENSORS & BIOELECTRONICS · 2022 · IF 12.545

Development of a sensitive phage-mimotope and horseradish peroxidase based electrochemical immunosensor for detection of O,O-dimethyl organophosphorus pesticides

Ruirui Shi,Wenting Zou,Zhiling Zhao,Guanqun Wang,Min Guo,Shiyun Ai,Qing Zhou,Fengchun Zhao,Zhengyou Yang

In this work, a green, harmless and signal-amplified electrochemical immunosensor based on phage-mimotope M31 (C–P-D-G-N-H-V-P-F-C) and horseradish peroxidase (HRP) was constructed for detecting O,O -dimethyl organophosphorus pesticides (OPs). The glassy carbon electrode (GCE) was modified by nitrogen and boron doped carbon quantum dots and graphene oxide (NBCQDs@GO) which can provide sufficient surface area and enhance the conductivity of the electrode. The O,O -dimethyl OPs class specific antibody mAb3C9 was assembled onto the NBCQDs@GO and the phage-mimotope M31 competitively bound to mAb3C9 with OPs. Furthermore, large amounts of anti-M13 mAb-HRP were introduced to the electrode through thousands of binding sites on the capsid of phage. HRP can catalyze 4-chloro-1-naphthol (4-CN) to produce insoluble precipitates (Benzo-4-chlorhexanedione, 4-CD). Hence, the concentration of OPs can be quantified by measuring impedance signal with electrochemical impedance spectrum (EIS). Under the optimal detection conditions, the 50% inhibitory concentration (IC 50 ) and limits of detection (LODs) values of 9 O,O -dimethyl OPs were in range of 0.989–4.017 ng/mL and 0.003–0.014 ng/mL, respectively. The recovery rates of spiked OPs in cucumber, cabbage and lettuce were 88.20–112.50% with coefficient of variation from 2.97 to 15.64%. Therefore, the immunosensor showed very good sensitivity and demonstrating potential application for the detection of O,O -dimethyl OPs in food samples.

CAS / MDL: 25952-53-8 106627-54-7
研究领域: 分析化学 · 环境科学 · 食品科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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CHEMICAL COMMUNICATIONS · 2017 ·Vol. 53 ·期 74 ·10295-10298 · IF 6.319

Regioselective hydrogenolysis of aryl ether C–O bonds by tungsten carbides with controlled phase compositions

Huihuang Fang,Junmou Du,Chenchen Tian,Jianwei Zheng,Xinping Duan,Linmin Ye,Youzhu Yuan

Evenly dispersed tungsten carbides with controlled phase compositions that exhibit an impressive capacity to carry out the regioselective hydrogenolysis of inert aryl ether C–O bonds instead of aliphatic C–O bonds to produce aromatic compounds are reported.

CAS / MDL: 12070-12-1 12070-13-2
研究领域: 催化 · 有机化学 · 材料科学
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INORGANIC CHEMISTRY · 2025 · IF 4.7

Chelating 1,2-Bis(2′-picolyl)-o-carborane as a Supporting Ligand for Pd-Catalyzed Selective B(3,6)–H Difunctionalization of o-Carboranes

Qiang-Qiang Ma,Peng Zhou,Yizhen Liu,Zuowei Xie

Transition metal catalyzed selective cage B–H functionalization of carboranes has made significant progress in recent years, giving rise to the efficient synthesis of a large variety of cage B-functionalized carboranes including alkenylation, arylation, alkynylation, borylation, hydroxylation, acyloxylation, amination, and halogenation. However, the mechanisms of these catalytic B–X coupling reactions are not well understood. Herein, we describe the isolation and characterization of the catalytically relevant o-carborane based palladium(II) metallacycle, disclosing the details of Pd-catalyzed B–H functionalization of o-carboranes. As a result, highly selective catalytic B(3,6)-dihalogenation, -dimethylation, and -diarylation of o-carboranes have been achieved.

CAS / MDL: 6959-47-3
研究领域: 有机化学 · 过渡金属催化 · 材料化学
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SEPARATION AND PURIFICATION TECHNOLOGY · 2022 · IF 9.136

Constructing the multilayer O-g-C3N4@W18O49 heterostructure for deeply photocatalytic oxidation NO

Xiaoyan Li,Rui Zhao,Hongfang Li,Jing Jiang,Lunhong Ai,Xuejuan Cao,Juanli Liu,Hanjun Zou,Youyu Duan

Suffering from inefficient separation and transfer of photogenerated carriers, the deeply photocatalytic oxidation of NO-to-NO 3 – over g-C 3 N 4 is still a daunting challenge. Well-designed heterojunction photocatalysts have been proven to be effective in steering charge transfer for achieving a particular migration path and more active sites, which hold huge promise in further performance stimulation. Herein, in-situ face-to-face hydrothermal approach is developed to prepare a multilayer heterostructure O doping g-C 3 N 4 (O-g-C 3 N 4 ) with W 18 O 49 (O-g-C 3 N 4 @W 18 O 49 ). The experimental and theoretical results show that the unique multilayer heterostructure can improve the separation efficiency of carriers by changing the electron migration path. Moreover, doping O atoms are identified as the newly formed active centers to largely facilitate the activation of NO. Impressively, the O-g-C 3 N 4 @W 18 O 49 photocatalyst thus exhibits largely improved photocatalytic NO removal rate (56.7 %, 0.1 g of sample) and high selectivity of NO to NO 3 – (98.3 %). It outperforms the reported photocatalysts materials in visible light. This study not only provides a facile strategy for experimentally screening advanced photocatalytic materials, but also paves the way for the deep oxidation of NO.

研究领域: 材料科学 · 环境科学 · 催化化学
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FUEL · 2024 · IF 6.7

Self-hydrogen transfer hydrogenolysis of β-O-4 bonds in lignin model compounds over NiCu/Al2O3 catalyst

Fa-Peng Wu,Le-Le Qiu,Yun-Peng Zhao,Zong-Pin Fu,Jing Liang,Jian Xiao,Jian Li,Fang-Jing Liu,Jing-Pei Cao

Hydrogenolysis of β-O-4 linkages in lignin to produce aromatic compounds is attractive but challenging. Currently, external hydrogen source like hydrogen gas or hydrogen-donor solvent is necessary during hydrogenolysis, leading to high cost and low selectivity of products. Herein, a NiCu/Al 2 O 3 catalyst was prepared for self-hydrogen transfer hydrogenolysis (SHTH) of C β -O bond using inherent C α H-OH structure as H-source. A β-O-4 model compound, 2-phenoxy-1-phenethanol, was completely transformed into acetophenone and phenol at 220 ℃ under 1 MPa N 2 for 2h. The SHTH reaction proceeded through a dehydrogenation reaction followed by a hydrogenolysis reaction. Hydrogen radicals released from C α H-OH group generated a “hydrogen pool” on the catalyst surface, which inserted into the formed β-O-4 ketone intermediate to cleave the C β -O bond. The catalyst presented outstanding reusability and universality during the SHTH reaction. Moreover, the methoxy groups at aryl positions impeded the SHTH process, and the steric effect was related to the amount and position of methoxy groups. This study realizes the utilization of structural hydrogen from lignin model compounds for its C β -O bond cleavage , providing an economical and sustainable method toward lignin valorization.

研究领域: 化学工程 · 可再生资源利用
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2021 · IF 4.539

Potential application of novel amphiphilic Janus-SiO2 nanoparticles stabilized O/W/O emulsion for enhanced oil recovery

Han Jia,Jiajun Dai,Lingchun Miao,Xin Wei,Hongtao Tang,Pan Huang,Haidong Jia,Juan He,Kaihe Lv,Dexin Liu

The Janus nanoparticles stabilized Pickering emulsions showed great application potential in various fields, including enhanced oil recovery (EOR). In this study, the amphiphilic Janus-SiO 2 nanoparticles (Janus-C12) are successfully synthesized by the Pickering emulsion method and characterized by Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), ζ-potential and contact angle measurements. The phase inversion from oil-in-water (O/W), multiple oil-in-water-oil (O/W/O) emulsion, to water-in-oil (W/O) emulsions was observed with the delicate control for the modification degrees of Janus-C12. The possible emulsification mechanisms for various Janus-C12 stabilized emulsions were proposed. The multiple O/W/O emulsion stability in harsh conditions and the influence factors (nanoparticles concentration, water/oil volume ratio and NaCl concentration) were studied systematically. Moreover, the Janus-C12–79% stabilized multiple O/W/O Pickering emulsions exhibited excellent EOR performance (additional oil recovery of 27.2%) in core flooding tests, and the possible EOR mechanism was explored via microscopic visualization experiments.

研究领域: 化学工程 · 材料科学 · 石油工程
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APPLIED CATALYSIS B-ENVIRONMENTAL · 2021 · IF 19.503

N,O-C Nanocage-mediated high-efficient hydrogen evolution reaction on IrNi@N,O-C electrocatalyst

Shanyong Chen,Shiyan Wang,Panpan Hao,Muhong Li,Yu Zhang,Jia Guo,Weiping Ding,Min Liu,Jinlan Wang,Xuefeng Guo

Development of high-performance and stable electrocatalysts for hydrogen evolution reaction (HER) is crucial for hydrogen economy. Inspired by hydrogen evolution behavior on hydrogenase enzyme, in which the azadithiolate bridging ligand of active center facilitates fast proton shuttling and catalytic turnover, here we present an efficient approach to enhance both HER kinetics and stability realizing on an IrNi@N,O-C catalyst with individual IrNi nanoparticle separately confined in N and O co-doped carbon (N,O-C) nanocage. Experimental and theoretical investigations indicate that the N,O-C nanocage provides proton-adsorbing functionality on raising H* coverage over IrNi active centers, resulting in much accelerated HER kinetics. The IrNi@N,O-C presents superior HER performances compared to all reported Ir-based catalysts, with overpotential of 22 mV at 100 mA cm −2 , ultrahigh mass activity of 9.82 A mg Ir −1 (−0.050 V vs. RHE) and outstanding durability of 200 h at large current density. This work affords fresh insights/strategies for design of high-performance electrocatalysts

研究领域: 材料科学 · 电化学
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