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ADVANCED SYNTHESIS & CATALYSIS · 2019 ·Vol. 361 ·期 13 ·3191-3199 · IF 5.451

Chemoenzymatic Approach to (S)-1,2,3,4-Tetrahydroisoquinoline Carboxylic Acids Employing D-Amino Acid Oxidase

Shuyun Ju,Mingxin Qian,Gang Xu,Lirong Yang,Jianping Wu

Optically pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids constitute an important class of building blocks for the synthesis of natural products and synthetic pharmaceuticals. However, redox deracemization of racemic 1,2,3,4-tetrahydroisoquinoline carboxylic acids as an attractive method is still challenging for the lack of suitable oxidoreductases. Herein, a D-amino acid oxidase from Fusarium solani M-0718 ( Fs DAAO) with broad substrate scope and excellent enantioselectivity was exploited through genome mining, and applied for the kinetic resolution of a number of racemic 1- and 3-carboxyl substituted tetrahydroisoquinolines to yield the corresponding ( S )-enantiomers with excellent enantiomeric excess ( ee ) values (up to >99%). By using Fs DAAO in combination with ammonia-borane in one pot, deracemization of these racemic carboxyl-substituted tetrahydroisoquinolines was achieved with conversions up to >98% and >99% ee . Preparative-scale deracemization of racemic 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid and 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid was also demonstrated with good isolated yields (82% and 73%, respectively) and ee >99%. Our study provides an effective method for the synthesis of enantiomeric pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids. This method is expected to provide access to chiral carboxyl-substituted 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro-ß-carbolines.

研究领域: 生物化学 · 有机合成 · 酶工程
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FOOD HYDROCOLLOIDS · 2025 · IF 12.4

Vitamin D-Loaded Microcapsule-Cod Protein Composite Gels: Texture, oral processing, and digestive properties

Yue Wang,Xiliang Yu,Weiping Zhao,Shiyi Liu,Sangeeta Prakash,Xiuping Dong

This study developed a functional gel system based on cod protein, incorporated with vitamin D-loaded bilayer microcapsules, to achieve both texture softening and nutritional enhancement through controlled moisture regulation and composite ingredients. Results demonstrated that the incorporation of microcapsules (5%-30%) significantly reduced cooking loss, gel strength, hardness, and gumminess, while improving whiteness ( p <0.05). Composite gels with 5%-15% microcapsules met the Level 6 (soft & bite-sized) criteria according to the International Dysphagia Diet Standardisation Initiative (IDDSI) testing, indicating their suitability for individuals with dysphagia. Particularly, the microcapsule content of 15% was identified as optimal. Microscopic observations confirmed that the microcapsules remained intact and demonstrated improved protein cross-linking, attributable to the addition of microcapsules enhancing hydrophobic interactions. However, excessive incorporation (30%) disrupted the three-dimensional network architecture of the gel. In vitro digestion results indicated that the soft gels with 15% microcapsules achieved a high protein digestibility of 91.83% and enhanced vitamin D bioaccessibility, compared to the free-form vitamin D with release rate of 57.46%. Furthermore, the composite gels with 15% microcapsules exhibited improved oral processing properties, including lower friction coefficient and reduced masticatory force, fulfilling both swallowing safety and nutritional requirements for populations with special dietary needs.

CAS / MDL: 67-97-0
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CHEMICAL PHYSICS LETTERS · 2021 · IF 2.328

Fast hydrogen detection by Pd(II)@alkyne-PVA/d-Ti3C2Tx composite at room temperature

Dongxin He,Wei Cao,Deshun Huang,Haimin Li,Jing Zhu,Pengxiang Zhao

Safety use of hydrogen leads to the development of highly sensitive materials for hydrogen sensing. Herein, Pd(II)@alkyne-PVA/ d -Ti 3 C 2 T x composite was prepared by spin-coating Pd(II)@alkyne-PVA solution onto the filter membrane supported with delaminated Ti 3 C 2 T x ( d -Ti 3 C 2 T x ). The properties of the composite were characterized using X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray (EDX) spectroscopy, and X-ray photoelectron spectroscopy (XPS). The results demonstrate that the composite shows high sensitivity and stability for hydrogen sensing.

研究领域: 材料科学 · 化学工程 · 纳米技术
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JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC · 2013 · IF 2.823

Chemoenzymatic synthesis of d-biotin intermediate lactone via lipase-catalyzed desymmetrization of meso diols

Jian-Yong Zheng,Sheng-Fan Wang,Yin-Jun Zhang,Xiang-Xian Ying,Yu-guang Wang,Zhao Wang

A chemoenzymatic methodology for the asymmetric synthesis of d -biotin intermediate lactone ((3a S , 6a R )-tetrahydro-1,3-dibenzylhexahydro-1 H -Furo[3,4-d] imidazole-2,4-dione) 1 has been demonstrated. The key step of the synthetic routes is Lipozyme RM IM catalyzed desymmetrization of meso-diols 3 . The highest enantiomeric excess ( e.e.   >   98%) and yield (>90%) of the product was achieved with Lipozyme RM IM in Dioxane/Toluene (1:3, v/v) at 35   °C. Furthermore, Lipozyme RM IM showed an excellent operational stability, retaining above 80% of the initial activity after 10 cycles of reaction. d -Biotin intermediate lactone 1 was obtained subsequently by Jones oxidation, basic hydrolysis and lactonization.

研究领域: 生物化学 · 有机合成 · 酶工程
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ADVANCED FUNCTIONAL MATERIALS · 2015 ·Vol. 25 ·期 18 ·2754-2762 · IF 11.805

Sunlight-Induced Cross-Linked Luminescent Films Based on Polysiloxanes and d-Limonene via Thiol–ene “Click” Chemistry

Yujing Zuo,Jinfeng Cao,Shengyu Feng

The increasing pursuit of biocontained elastic materials led the investigation of the potential use of the monoterpene limonene in film synthesis via thiol–ene reaction. Poly[(mercaptopropyl)methylsiloxane] (PMMS) is first synthesized. By controlling the molar ratio of PMMS and functional monomers, such as polyethylene glycol allyl methyl ether or rhodamine-B, PMMS is partially functionalized while leaving spare mercapto groups that could be further used as cross-linking sites. On the basis of the functionalized PMMS, novel transparent silicone luminescent films with hydrophilic tunable properties are prepared by natural-sunlight-triggered thiol–ene “click” chemistry by using d -limonene as a cross-linker. Their structures and properties are thoroughly characterized. Transparent luminescent films are coated on commercially available UV-light emitting diode (LED) cell from solution medium followed by an in situ cross-linking step; a colorful LED cell is obtained through this facile and efficient method. The UV-LED coated by films show very intense photoluminescence under normal visible light or the light is on, and has very high coloric purity.

研究领域: 材料科学 · 化学工程
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FOOD CHEMISTRY · 2024 · IF 8.5

A simple strategy for d/l-carnitine analysis in food samples using ion mobility spectrometry and theoretical calculations

Cong Liu,Ying Zou,Manli Zhang,Chaoxian Chi,Di Zhang,Fangling Wu,Chuan-Fan Ding

This work presents a straightforward approach to the separation d / l -carnitine ( d / l -Carn) using ion mobility–mass spectrometry (IM-MS) and theoretical calculations. Natamycin (Nat) was used as separation reagent to interact with the Carn, metal ions (G) were employed as ligand, the resultant ternary complexes [ d / l -Carn + Nat + G] + were observed experimentally. IM-MS results revealed that d / l -Carn could be baseline separated via complex formation using Li + , Na + , K + , Rb + , and Cs + , with a maximum peak separation resolution (R p-p ) of 2.91; Theoretical calculations were performed to determine the optimal conformations of [ d / l -Carn + Nat + Li/K] + , and the predicted collisional cross section values were consistent with the experimental values. Conformational analysis was used to elucidate the enantiomeric separation of d / l -Carn at the molecular level via the formation of ternary complexes. Furthermore, quantitative analyses for the determination of the enantiomers were established with effective linearity and acceptable sensitivity. Finally, the proposed method was successfully applied in the determination of d / l -Carn in food samples.

CAS / MDL: 56-45-1
研究领域: 分析化学 · 食品科学 · 生物化学
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Food Science & Nutrition · 2019 ·Vol. 7 ·期 6 ·2043-2049 · IF 1.747

Effects of power ultrasound on the activity and structure of β-D-glucosidase with potentially aroma-enhancing capability

Yujing Sun,Li Zeng,Yuanzhong Xue,Tianbao Yang,Zongming Cheng,Peilong Sun

β- d -glucosidase can release aroma precursors to improve the flavor of plant food, but the hydrolysis efficiency of the enzyme is low; the purpose of this study was to improve the enzyme activity using ultrasound. The effects of ultrasound parameters on β- d -glucosidase activity were investigated, and the respective structures of enzyme activated and enzyme inhibited were further analyzed. Low temperature (20–45°C), low ultrasonic intensity (<181.53 W/cm 2 ), and short treatment time (<15 min) led to the activation of β- d -glucosidase, whereas high temperature (45–60°C), high ultrasonic intensity (>181.53 W/cm 2 ), and long treatment time (>15 min) led to its inhibition. Application of ultrasound lowered the optimum temperature for β- d -glucosidase activity from 50 to 40°C. Ultrasound did not change the primary structures of the enzyme, but changed the secondary structures. When ultrasound activated β- d -glucosidase, the α-helix contents were increased, the β-fold and irregular coil content were reduced. When ultrasound inhibited β- d -glucosidase, the contents of β-folds were increased, the α-helix and irregular coil contents were reduced.. In summary, activation or inhibition of β- d -glucosidase under ultrasound was determined by the ultrasound conditions. This study suggests that ultrasound combined with β-D-glucosidase can be used in aroma-enhancing.

CAS / MDL: 3150-24-1
研究领域: 食品科学 · 生物化学
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ChemistrySelect · 2022 ·Vol. 7 ·期 45 ·e202203721 · IF 2.307

Ratiometric Detection of Al Based on the Mixing of D-penicillamine-Functionalized Copper Nanoclusters with Pyridoxal 5’-phosphate

Weihua Yu,Jianhua Kuang,Qingqing Hu,Zhonghua Wang,Yunwen Liao,Zhengjun Cheng

Graphical A new ratio fluorescent probe (RF-probe) based on the mixing of red-emitting D-penicillamine (DPA) stabilized copper nanoclusters (DPA-CuNCs) with pyridoxal 5’-phosphate (PLP) was designed for sensitive and selective determination of Al 3+ . The excess accumulation of nonessential Al 3+ in the human body can cause serious health problems, thus there is significant interest in the detection of Al 3+ . A new ratio fluorescent probe (RF-probe) based on the mixing of red-emitting D-penicillamine (DPA) stabilized copper nanoclusters (DPA-CuNCs) with pyridoxal 5’-phosphate (PLP) was designed for sensitive and selective determination of Al 3+ . The −CHO group of PLP is expected to form an imine linkage with the free −NH 2 group available of the DPA on the surface of DPA-CuNCs. The content of Al 3+ could be mensurated by the as-prepared RF-probe with a linear response in the range of 1.33–46.67 μmol ⋅ L −1 , and corresponding limit of detection (LOD) was calculated to be 0.33 μmol ⋅ L −1 . Moreover, the RF-probe was successfully extended to the assay of Al 3+ in aluminum carbonate chewing tablets, baking powder, pond water and drink water with satisfactory results compared to the standard atomic absorption spectroscopy (AAS).

CAS / MDL: 52-67-5
研究领域: 分析化学 · 环境科学 · 生物医学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2014 · IF 2.129

A fluorescence detection of d-penicillamine based on Cu2+-induced fluorescence quenching system of protein-stabilized gold nanoclusters

Peng Wang,Bang Lin Li,Nian Bing Li,Hong Qun Luo

In this contribution, a luminescent gold nanoclusters which were synthesized by bovine serum albumin as novel fluorescent probes were successfully utilized for the determination of d -penicillamine for the first time. Cupric ion was employed to quench the strong fluorescence of the gold nanoclusters, whereas the addition of d -penicillamine caused obvious restoration of fluorescence intensity of the Cu 2+ -gold nanoclusters system. Under optimum conditions, the increment in fluorescence intensity of Cu 2+ -gold nanoclusters system caused by d -penicillamine was linearly proportional to the concentration of d -penicillamine in the range of 2.0   ×   10 −5 –2.39   ×   10 −4   M. The detection limit for d -penicillamine was 5.4   ×   10 −6   M. With the off–on fluorescence signal at 650   nm approaching the near-infrared region, the present sensor for d -penicillamine detection had high sensitivity and low spectral interference. Furthermore, the novel gold nanoclusters-based fluorescent sensor has been applied to the determination of d -penicillamine in real biological samples with satisfactory results.

CAS / MDL: 7365-45-9 77-86-1
研究领域: 分析化学 · 生物医学 · 纳米科技
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Materials Science & Engineering C-Materials for Biological Applications · 2017 · IF 4.164

Exploring the optimal ratio of d-glucose/l-aspartic acid for targeting carbon dots toward brain tumor cells

Lihong Qiao,Tingting Sun,Xiaohua Zheng,Min Zheng,Zhigang Xie

Targeting imaging to the desired site of action can increase the accuracy and effectiveness of diagnostic and treatment. In this work, a series of fluorescent carbon dots (CDs) were prepared by varying molar ratios of d -glucose (Glu) to l -aspartic acid (Asp). Their photophysical properties, morphologies and structures were investigated in detail. More important, the targeting ability was screened by confocal laser scanning microscopy and flow cytometry. The results indicate that CDs prepared from the optimal molar ratio of Glu/Asp (7:3) exhibit the highest targeting ability on C6 glioma cells. This work highlights the interplay of molecular design and corresponding functions, and open new possibility of developing state-of-art nanoparticles for biomedical applications.

CAS / MDL: 56-84-8 56570-89-9
研究领域: 生物医学 · 纳米材料 · 肿瘤学
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Frontiers in Materials · 2024 · IF 2.6

D-amino acid/gentamicin loaded zwitterionic hydrogel coatings with optimized mechanical stability and biofilm inhibition capabilities

Yang Jingzhi,Ran Yami,Zhao Junsen,Xing Taiwei,Hao Xiangping,Zhang Dawei

Biofilms associated bacterial infections on material surfaces have become a tremendous biomedical challenge. Developing antimicrobial coatings on biomaterial surfaces and endowing them with decent mechanical stability and biofilm inhibition capabilities is an efficient way to resist bacterial attachment and biofilm formation. Herein, we integrated 2-hydroxyethyl methacrylate (HEMA) and D-amino acid mixtures based antibiofilm combinations with sulfobetaine methacrylate (SBMA) hydrogel coatings. The obtained hydrogel coatings demonstrated high stability in various transport and service environments. The proper incorporation of the HEMA achieves only ∼3% weight loss of SBMA hydrogel coatings after swelling, flushing and abrasion damages. In addition, both biofilm formation inhibiting D-amino acid mixtures and bacteria-killing gentamicin components were loaded in the coatings. The synergistic action of these two components was able to significantly reduce the bacterial numbers with up to 2.3 log reduction. The bacteria exposed to D-amino acid mixtures was difficult to form biofilm, which was more susceptive to the harm of gentamicin. This work provides an effective paradigm to integrate mechanically stable SBMA-HEMA hydrogel with natural D-amino acid mixtures based antibiofilm agents to generate biomedical surfaces to combat biofilms associated bacterial infections.

研究领域: 生物材料学 · 感染生物学 · 医学工程
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APPLIED SURFACE SCIENCE · 2020 · IF 6.182

Tunable d-spacing of dry reduced graphene oxide nanosheets for enhancing re-dispersibility in organic solvents

He Chen,Chunhong Qi,Luyan Shen,Qiang Fu,Zhiqiang Wang,Zhiyuan Xiong,Youyi Sun,Yaqing Liu

The reduced graphene oxide (rGO) nanosheets were modified by using polymeric nanospheres to adjust the d-spacings between dry rGO nanosheets. The experimental and computational studies show that the incorporation of polymeric nanospheres can effectively increase the d-spacing between dry rGO nanosheets, and meanwhile provide good compatibility of rGO with organic solvents. Specifically, when the d-spacing between nanosheets is greater than 14.0 nm, the dried rGO nanosheets can be well redispersed and stabilized in various organic solvents. This study thus provides a new technology that can produce dry rGO nanosheets with good re-dispersibility and stability in various organic solvents on a large-scale in a more environmental friendly manner.

研究领域: 材料科学 · 化学工程
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