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CHEMICAL ENGINEERING JOURNAL · 2022 · IF 16.744

Recycling preparation of high-purity tagatose from galactose using one-pot boronate affinity adsorbent-based adsorption-Assisted isomerization and simultaneous purification

Zihao Wang,Mingming Wang,Xiaomei Lyu,Caiyun Wang,Yanjun Tong,Xiao Hua,Ruijin Yang

D -tagatose, one of the most valuable low-calorie rare sugars, is in huge market demand in the current food and medicine industries due to its excellent physiological functions. The production and recovery of high-purity tagatose from galactose isomerization presents two major challenges due to the exist thermodynamically limitation and their high structural similarity. Interestingly, the prepared macroporous polymeric boronate-affinity adsorbent (PBA-adsorbent) exhibited superior binding affinity towards tagatose than galactose. In a 1:1 galactose-to-tagatose binary solution, the PBA-adsorbent presented a much higher adsorption capacity towards tagatose ( Q Tag  = 53.94 mg/g) than galactose ( Q Gal  = 7.06 mg/g) and therefore enabled an excellent purification efficiency. Herein, a novel strategy for combining the PBA-adsorbent-based adsorption-assisted galactose-to-tagatose isomerization and simultaneous purification of tagatose, where the isomerization of galactose and the recovery of tagatose occur concurrently in the same PBA-adsorbent loaded column system, is presented. Through in situ selective capture of the newly formed tagatose, while leaving behind the galactose, the applied strategy enables an improved galactose-to-tagatose isomerization equilibrium with the yield of tagatose reaching up to 52.92%. Simultaneously, the adsorbed tagatose can be recovered efficiently via a two-stage sequential desorption process, which improves the tagatose purity to ∼ 85% with a promising recovery ratio of 87.42%. Remarkably, both the prepared PBA-adsorbent and the applied strategy exhibited excellent operational stability. Through pH-controlled desorption, the loaded PBA-adsorbent and the column system can be easily regenerated, well proving their good durability and recyclability in sustainable industrial applications. Furthermore, a possible mechanism involving the effect of boron-to-sugar ratio, the variation of boron intrinsic chemical states, and pH-responsive selective adsorption and sequential desorption was proposed to help understand how the applied PBA-adsorbent based strategy facilitates the highly efficient galactose-to-tagatose isomerization.

CAS / MDL: 67-68-5 87-81-0 59-23-4
研究领域: 食品科学 · 生物化学 · 工业化学
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CHINESE JOURNAL OF CHEMICAL ENGINEERING · 2021 · IF 3.171

Nickel-Carnosine complex: A new carrier for enzymes immobilization by affinity adsorption

Junyang Xu,Yanjun Jiang,Liya Zhou,Li Ma,Zhihong Huang,Jiafu Shi,Jing Gao,Ying He

Immobilization is an effective method to promote the application of enzyme industry for improving the stability and realizing recovery of enzyme. To some extent, the performance of immobilized enzyme depends on the choice of carrier material. Therefore, the development of new carrier materials has been one of the key issues concerned by enzyme immobilization researchers. In this work, a novel organic–inorganic hybrid material, nickel-carnosine complex (NiCar), was synthesized for the first time by solvothermal method. The obtained NiCar exhibits spherical morphology, hierarchical porosity and abundant unsaturated coordination nickel ions , which provide excellent anchoring sites for the immobilization of proteins. His-tagged organophosphate-degrading enzyme (OpdA) and ω-transaminase (ω-TA) were used as model enzymes to evaluate the performance of NiCar as a carrier. By a simple adsorption process , the enzyme molecules can be fixed on the particles of NiCar, and the stability and reusability are significantly improved. The analysis of protein adsorption on NiCar verified that the affinity adsorption between the imidazole functional group on the protein and the unsaturated coordination nickel ions on NiCar was the main force in the immobilization process, which provided an idea way for the development of new enzyme immobilization carriers.

CAS / MDL: 305-84-0
研究领域: 生物化学 · 材料科学 · 酶工程
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ANALYTICA CHIMICA ACTA · 2015 · IF 4.513

The preparation of high-capacity boronate affinity adsorbents by surface initiated reversible addition fragmentation chain transfer polymerization for the enrichment of ribonucleosides in serum

Chaozhan Wang,Huanhuan Xu,Yinmao Wei

Boronate affinity adsorption is uniquely selective for cis-diol-containing molecules. The preparation and application of boronate affinity materials has attracted much attention in recent years. In this work, a high-capacity boronate affinity adsorbent was prepared by surface-initiated reversible addition–fragmentation chain transfer polymerization (SI-RAFT). Commercial aminated poly(glycidyl methacrylate) (PGMA) microspheres were modified with the chain transfer agent (CTA) S-1-dodecyl-S-(α,α-dimethyl-α-acetic acid)trithiocarbonate (DDATC). Boronate-affinity adsorbents were then prepared via SI-RAFT polymerization employing 3-acrylamidophenylboronic acid (AAPBA) as the monomer . The Fourier transform infrared spectroscopy (FT-IR), nitrogen adsorption and desorption measurements have proven the successful grafting of AAPBA on PGMA microspheres surface. The boronate affinity adsorbents thus prepared possess much higher adsorption capacity (99.2 µmol/g of adenosine) and both faster adsorption and desorption speed towards ribonucleosides , the adsorption and desorption could be completed in 2 min. The high selectivity of the adsorbents to ribonucleosides was verified in the presence of a large excess of deoxynucleosides. The boronate affinity adsorbents were then employed for sample pretreatment before HPLC analysis of ribonucleosides in serum. The ribonucleosides were effectively enriched by boronate affinity dispersive solid-phase extraction (BA-DSPE), with high mass recoveries and good precision. The simultaneous determination of uridine and guanosine in calf serum was achieved by utilizing the standard addition method, their contents were determined to be 170 ± 11.6 ng/mL and 39.6 ± 4.4 ng/mL respectively. The results proved that the prepared boronate affinity materials could be applied for sample pretreatment of cis-diol containing molecules in biological samples.

研究领域: 分析化学 · 生物医学
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Analytical Methods · 2018 ·Vol. 11 ·期 3 ·317-326 · IF 2.073

A new boronate-affinity hollow solid phase extraction adsorbent for the enrichment of cis-diol-containing isoflavones in soybean milk samples

Xingyu Hou,Wei Huang,Fugui Zhu,Fang Geng,Miaomiao Tian

In this study, a new boronate-affinity hollow adsorbent was successfully fabricated. This adsorbent was prepared using mesoporous MCM-48 as a sacrificial support, methacrylic acid (MAA), N,N-methylenebisacrylamide (MBA) and azobisisobutyronitrile (AIBN) were applied as a functional monomer, cross-linker and initiator, respectively, and further modified with boronic acid groups (4-vinylphenylboronic acid, VPBA) to improve the enrichment efficiency. Such materials were composed of a hollow structure, a hydrophilic polymer coating of poly(MBA-MAA), and a VPBA-functionalized shell designed for capturing isoflavones. The resulting material coupled with high-performance liquid chromatography (HPLC) was applied to analyze three cis-diol isoflavones (daidzin, glycitin, and genistin) in soybean milk samples. The sorbent was characterized by transmission electron microscopy, Fourier transform infrared spectrometry and thermo-gravimetric analysis. Several parameters affecting the extraction efficiency were optimized. Owing to the hollow structure, more binding sites were located on the inner and outer surfaces of this material, which could facilitate the binding of the target molecules to the adsorbent. Adsorption selectivity studies indicated that the prepared material can selectively recognize isoflavones. Under optimized conditions, the limits of detection of the method were 3.8 to 7.3 μg L−1 for the three isoflavones based on a signal-to-noise ratio of 3 : 1. The spiked recoveries were found to be between 67.4 and 104.7% (the relative standard deviations were less than 3.8%, n = 3). This indicated the superiority of the method in selective extraction of isoflavones even from complex matrices.

研究领域: 分析化学 · 食品科学
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BIOMEDICAL CHROMATOGRAPHY · 2015 ·Vol. 29 ·期 8 ·1133-1136 · IF 1.723

Boronate affinity adsorption of cis-diol-containing biomolecules in nonaqueous solvent

Li Zhang,Chaozhan Wang,Yinmao Wei

Boronate affinity has attracted much attention in recent years. It has been broadly used for selective isolation and enrichment of cis -diol-containing molecules. Conventionally, the cis -diols are adsorbed in mild alkaline aqueous solutions. In this work, for the first time, we found that boronate affinity adsorption could also be performed in nonaqueous solvent at nonbasic pH. Cis -diol-containing compounds present in herbal medicines were used for the adsorption test. The results indicated that all compounds obtained higher recoveries in the organic solvents (methanol, acetonitrile, ethyl acetate) compared with alkaline buffer. The adsorption of vicinal cis -diol-containing molecules in organic solvents could be accomplished rapidly, with high selectivity and high recoveries (>80%). These results shed light on the possibility of boronate affinity adsorption in nonaqueous solvents. The results are very important for the isolation and enrichment of cis -diols, which have poor solubility in water, especially for those in herbal medicines. Copyright © 2015 John Wiley & Sons, Ltd.

研究领域: 生物化学 · 药物化学
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GREEN CHEMISTRY · 2015 ·Vol. 18 ·期 7 ·2147-2154 · IF 8.02

An efficient enzymatic production of N-acetyl-D-glucosamine from crude chitin powders

Alei Zhang,Cong Gao,Jing Wang,Kequan Chen,Pingkai Ouyang

In this study, we present an efficient affinity adsorption–enzymatic reaction integrated approach to produce N-acetyl-D-glucosamine (GlcNAc) from crude chitin powders (CP). Chitinase was first purified from the crude enzyme mixture by affinity adsorption on the CP substrate, with ∼92.7% recovery of the enzyme achieved within 10 minutes in the presence of 20 g L−1 of CP under optimized conditions. The chitinase then efficiently converted 40 g L−1 of CP to 39.3 g L−1 of GlcNAc in a batch enzymatic reaction for 4 days, achieving nearly 100% conversion of the substrate CP. The product GlcNAc was easily separated from hydrolysates after destaining, concentrating, crystallizing and drying processes with a high purity of 98%. In addition, the chitinase can be conveniently reused for several batches by the affinity adsorption–enzymatic reaction approach, giving an average yield of 29.6 g L−1 of GlcNAc based on 30 g L−1 of CP as the substrate.

研究领域: 生物化学 · 酶工程
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JOURNAL OF THE CHINESE CHEMICAL SOCIETY · 2018 ·Vol. 65 ·期 9 ·1090-1097 · IF 0.862

Facile preparation of a high-capacity boronate-affinity adsorbent based on low-cost commercial supports for selective enrichment of cis-diol-containing biomolecules

Chunyan Li,Chaozhan Wang,Yinmao Wei

Boronate-affinity adsorbents have been regarded as favorable extraction adsorbents for the pretreatment of cis -diol-containing biomolecules owning to their specific selectivity, but most of them have low adsorption capacity and a tedious synthesis methods. In this study, a new boronate-affinity material (PGMA@FPBA) with high adsorption capacity was synthesized via a “one-pot” method based on a low-cost commercial support. The PGMA@FPBA was characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray photoelectron spectroscopy (XPS), scanning electron microscope (SEM), and nitrogen adsorption/desorption measurements. The as-prepared adsorbent showed good selectivity, high adsorption capacity (448 μmol/g for catechol), and fast adsorption equilibration (1 min) for cis -diol-containing biomolecules. Subsequently, as an example for application, the obtained PGMA@FPBA was used as a dispersive solid-phase extraction (d-SPE) adsorbent for enrichment of quercetin in red wine. The results indicated that the facile-prepared boronate-affinity adsorbent has great potential application for separation and enrichment of cis -diol-containing biomolecules in complex samples.

研究领域: 分析化学 · 生物化学
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JOURNAL OF HAZARDOUS MATERIALS · 2022 · IF 14.224

Facile preparation of uniform-sized covalent organic framework nanoflowers as versatile sample-pretreatment platforms for sensitive and specific determination of hazardous substances

Chun-Yang Li,Shi-Wen Lv,Lu Yang,Jin Wang,Jing-Min Liu,Shuo Wang

Covalent-organic frameworks (COFs) have lately received extensive interest for their outstanding performance, especially to adsorption of hazards, while easy-preparation of uniform-sized COFs hold a great challenge. This research presented a simple synthesis method of flower-shaped COF (nanoflower) with strong hydrophobic surface at room temperature. Taking advantage of its easy-prepared and uniform-sized features, we proposed a versatile and efficient sample-pretreatment platform by employing the nanoflower COF for affinity adsorption of various hydrophobic biotoxins and further surface imprinting for selective enrichment of specific biotoxin (COF@MIP), respectively. The COF@MIP was integrating COF with molecular imprinting technique to achieve selective identification of sterigmatocystin (ST) with high specificity and sensitivity. They both exhibited well reusability, preserving 81% of initial activity after being used for six cycles. The as-prepared materials coupled with offline solid phase extraction (SPE) and high performance liquid chromatography (HPLC) were successfully applied to five common cereals with good recoveries in the range of 70.3–100.7%. Moreover, the principle of versatile sample pretreatment and detection platform based on the facile-prepared and uniform-sized COF nanoflower would be easily extended to other hazards. It provided a prospective approach for the pretreatment and determination of hazardous substances with low level in complex sample matrix.

研究领域: 分析化学 · 环境科学 · 食品安全
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CHINESE JOURNAL OF ANALYTICAL CHEMISTRY · 2020 · IF 0.936

Graphene Oxide-based Magnetic Boronate-affinity Adsorbent for Extraction of Horseradish Peroxidase

Xing-Yu HOU,Yu-Kui TONG,Fu-Gui ZHU,Qin-Fei XIA,Miao-Miao TIAN

Graphene oxide (GO) is a two-dimensional atom-thick sheet generated from an oxidation of graphene. GO possesses a range of reactive oxygen functional groups on the basal planes and edges, which makes it a good candidate in the field of separation and enrichment through chemical functionalization. In this work, GO-based Fe 3 O 4 magnetic nanoparticles were prepared, and boronic acid groups were introduced by 3-aminophenylboronic acid (APBA) at the same time to improve the enrichment efficiency. Herein, the GO-based magnetic boronate-affinity adsorbent (Fe 3 O 4 @GO@APBA) was developed focusing on the specific capture of low abundance of glycoprotein. The composites gathered excellent characters of large specific surface area and biocompatibility of GO, strong magnetic responsiveness, and enhanced affinity properties of boronic acid. The proposed system showed better specificity for glycoprotein even in the presence of non-glycoproteins. As a result, the prepared Fe 3 O 4 @GO@APBA not only exhibited high selectivity for horseradish peroxidase (HRP), and an outstanding tolerance for interference, but also showed excellent rebinding rate for an extraction application. Furthermore, this method provided a reliable way to improve conventional magnetic adsorbent, and showed great potential in analysis of low-abundant glycoprotein from even complex samples.

研究领域: 生物化学 · 分析化学
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RSC Advances · 2016 ·Vol. 6 ·期 85 ·82309-82320 · IF 3.289

Synthesis of a phenylboronic acid-functionalized thermosensitive block copolymer and its application in separation and purification of vicinal-diol-containing compounds

Yun Wang,Yuanyuan Li,Juan Han,Xu Tang,Liang Ni,Xiaowei Hu,Lei Wang

A phenylboronic acid-functionalized amphiphilic thermosensitive block copolymer was prepared by taking PEO20PPO60PEO20 as the template and a detailed study of its performance in downstream separation processes was presented. Alizarin red was used as the model compound to study the feasibility of using an affinity adsorption system and aqueous two-phase flotation system based on the phenylboronic acid-functionalized PEO20PPO60PEO20 for the separation and purification of ortho-hydroxyl compounds. The optimized conditions of the affinity adsorption experiment were: 2% phenylboronic acid-functionalized PEO20PPO60PEO20, 0.3 mg alizarin red, 40% K2HPO4 and 4 h adsorption time. The affinity adsorption rate of alizarin red reached 98% under such conditions. In addition, a flotation recovery of alizarin red of 97% was obtained under the optimal conditions of aqueous two-phase flotation: 0.3 g of collector, 12 g K2HPO4, 0.6 mg alizarin red, 15 mL min−1 nitrogen flow rate and 40 min flotation time. Both methods are capable of separating alizarin red, suggesting their broad application prospect in downstream separation engineering of vicinal-diol-containing compounds.

CAS / MDL: 25487-66-5
研究领域: 化学工程 · 分离纯化技术 · 高分子材料科学
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ANALYTICA CHIMICA ACTA · 2016 · IF 4.712

Facile synthesis of a boronate affinity sorbent from mesoporous nanomagnetic polyhedral oligomeric silsesquioxanes composite and its application for enrichment of catecholamines in human urine

Haibo He,Ziqing Zhou,Chen Dong,Xin Wang,Qiong-wei Yu,Yunyi Lei,Liqiang Luo,Yuqi Feng

A boronate-decorated nanomagnetic organic-inorganic hybrid material was facilely synthesized by utilizing the nanomagnetic polyhedral oligomeric silsesquioxanes (POSS) composite (Fe 3 O 4 @POSS) as the base platform. A simple copolymerization occurred between 3-acrylamidophenylboronic acid (AAPBA) and the residual end vinyl groups supplied by the substrate. Here the special emphasis was placed on the octavinyl POSS, which not only acted as the building blocks for a hybrid architecture but also facilitated the process of grafting boronate groups onto the surface of POSS based nanomagnetic composite (Fe 3 O 4 @POSS). The successful immobilization of affinity ligand-AAPBA on the Fe 3 O 4 @POSS was confirmed by Fourier transform infrared (FT-IR), elemental analysis , inductively coupled plasma atomic emission spectrometer (ICP-AES), field emission scanning electron microscope . A magnetic solid-phase extraction (MSPE) for cis -diols enrichment was developed using the as-prepared Fe 3 O 4 @POSS-AAPBA material as an affinity sorbent and three catecholamines (CAs), namely noradrenaline, epinephrine and isoprenaline , as model analytes. Under the optimal extraction conditions, sensitive and simultaneous analysis of three CAs from the urine sample was achieved by high-performance liquid chromatography with UV detection (HPLC-UV). The limits of detection (LOD, S/N = 3) and the limits of quantitation (LOQ, S/N = 10) for the target analytes were 0.81–1.32 ng mL −1 and 2.70–4.40 ng mL −1 , respectively. Also good recoveries (85.5–101.7%) and repeatability (RSD≤10.1%) were obtained by this method. This work not only showed a facility for the utilization of Fe 3 O 4 @POSS as a substrate for constructing a boronate functionalized nanomagnetic sorbent , but also demonstrated the capability of the derived material for recognition of trace amount of cis -diols biomolecules presented in complicated biological matrices.

研究领域: 分析化学 · 生物医学工程
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ACS Omega · 2025 · IF 4.3

Nickel-Functionalized Nanoporous Heterostructure Microparticles for Immunoglobulin G Adsorption and Separation with High Efficiency

Yang Zhang,Wanting Zhang,Jin Li,Jiaxin Han,Xiangyang Gong,Mengmeng Wang

Developing advanced affinity adsorbents for immunoglobulin G (IgG) selective separation and purification is vital for clinical diagnosis and therapy. However, high-cost and low-specificity methods hinder high-purity IgG production. This work has fabricated nanoporous heterostructure microparticles by emulsion polymerization of styrene, divinylbenzene, and acrylic acid on the surface of sulfonated polystyrene particles. Following modification with nickel ions, the Ni2+-functionalized sulfonated poly(styrene-divinylbenzene)-poly(acrylic acid) (SPSDVB-PAA-Ni) exhibits dense nanoporous heterostructures and Ni2+-chelating sites, enabling electrostatic attraction and metal affinity interactions for the adsorption and separation of IgG. The SPSDVB-PAA-Ni affinity adsorbent demonstrates a high adsorption capacity of 192.7 mg·g–1 with rapid equilibration within 30 min, outperforming protein A/G adsorbents. Furthermore, the separation/purification of IgG from human serum samples is successfully achieved with a recovery of 73.7% and a purity of 83.7%. The study presents the SPSDVB-PAA-Ni polymer microparticles as promising adsorbents for selectively separating antibody drugs, suggesting their potential applications in clinical analysis.

CAS / MDL: 10101-97-0 9002-89-5
研究领域: 材料科学 · 生物医学工程 · 生物化学 · 高分子科学 · 免疫学
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