JOURNAL OF CHEMICAL AND ENGINEERING DATA
·
2026
·
IF 2.4
Qi Zhengfeng,Mao Caiyun,Xu Kai,Zhang Nan,Zhang Wentao,Jiang Ming,Zhang Qinqin,Feng Mi,Xu Fei
This
study examines the effect of chiral centers on the physicochemical
properties and solvation behavior of deep eutectic solvents (DESs)
prepared from chiral or racemic acids and standard hydrogen-bond acceptors
(HBAs). Circular dichroism spectroscopy, nuclear magnetic resonance
spectroscopy, and Fourier transform infrared spectroscopy analyses
confirmed retention of hydrogen-bond donors (HBDs) chirality and revealed
chirality-dependent hydrogen-bonding networks. DESs showed acidic
pH (1.81–2.68), high densities (1.13392–1.35126 g·cm –3 ) and viscosities (16.940–1340.900 mPa·s)
dependent on HBA/HBD type, ratio and chirality, with D-type DESs generally
exhibiting higher density and viscosity. Microcrystalline cellulose
(MCC) solubility (1.8–59.5 wt %) generally increases with solvent
H-bond donor ability and polarity. d -glucose in aqueous DES
solutions exhibited pronounced chirality-dependent solvation with
ethylene glycol: l -malic acid ( n : n = 4:1) displayed higher limiting apparent molar volumes
( V ϕ 0 = 115.39 to 118.38
× 10 –6 m 3 ·mol –1 ) and negative concentration coefficients ( S v = −10.34 to −13.76 × 10 –6 m 3 ·mol –2 ·kg), whereas ethylene
glycol: d -malic acid ( n : n = 4:1) had lower V ϕ 0 (90.58–103.39 × 10 –6 m 3 ·mol –1 ) and positive S v (15.58–49.45 × 10 –6 m 3 ·mol –2 ·kg) reflecting weaker, less ordered
solvation. This correlates with their MCC solubilities, with 4EG:L-Mac
and 4EG:D-Mac achieving 59.5 and 44.7 wt %, respectively. Overall,
DES properties and solute–solvent interactions are governed
by hydrogen bonding and stereochemistry, informing chiral solvent
design for biomass processing.
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MICROCHEMICAL JOURNAL
·
2025
·
IF 5.1
Xi-Meng Li,Bei-Ni Chen,Zheng-Quan Nie,Jian-Mei Yang,Jun-Nan He,Tong Yang,Jun-Hui Zhang,Jin-Xin Yang,Lei Zhang,Yan Zhao,Yue Sun,Jin Zhang
The precise determination of enantiomeric purity for mandelic acid ( D/L -MA), a chiral drug precursor, is crucial for the synthesis efficiency and efficacy of related chiral pharmaceuticals. High-performance liquid chromatography (HPLC) currently serves as a mainstream method for enantiomeric purity analysis, yet it suffers from some limitations, such as complicated sample pretreatment, long analysis cycles, and dependency on specialized equipment and operators. In this study, an electrochemical detection platform based on L -cysteine-stabilized gold nanoprobes was constructed, enabling effective analysis of MA enantiomer ratios. The sensor showed good selectivity for MA over its analogs. It also exhibited favorable enantioselectivity for D/L -MA, with a selectivity coefficient ( K D − MA / L − MA ) of 4.3. The limit of detection (LOD) for D -MA was determined to be 0.023 μM. Furthermore, this method showed good quantitative precision for real enantiomer mixtures at different ratio; the relative error is less than 5.4 % compared to reference measurements by HPLC. Density functional theory (DFT) calculations further reveal that the binding energy difference between L -MA and D -MA with the sensing interface reaches 34.9 kcal/mol (−7.3 kcal/mol vs. −42.2 kcal/mol). This stereospecific interaction regulates interfacial electron transfer kinetics to achieve enantiomeric discrimination. This study provides an electrochemical strategy integrating experimental and theoretical analyses for the purity assessment of chiral drug precursors, demonstrating the application potential in chiral drug synthesis and pharmaceutical quality control.
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NEW JOURNAL OF CHEMISTRY
·
2022
·Vol. 47
·期 2
·828-837
·
IF 3.925
Tiantian Wan,Zulei Zhang,Hailong Wang,Yiwen Yang,Hanxing Yang,Jian Zhang,Yanbo Zeng,Lei Li,Jinchun Li
Chlorogenic acid (CGA), a cis-diol-containing compound, exhibits anti-inflammatory, antiviral, antimicrobial and anti-oxidation properties. Thus, selective determination of CGA in food products is extremely necessary. In this study, a boron affinity magnetic polymer named Fe3O4@SiO2@PIL was synthesized to detect the concentration of CGA in actual fruit samples. The Fe3O4@SiO2@PIL was characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), Fourier transform infrared (FT-IR) spectroscopy, X-ray photoelectron spectroscopy (XPS) and thermogravimetric (TG) analysis. The results showed that the Fe3O4@SiO2@PIL has uniform morphology, good magnetic properties, suitable structure and high stability. The experimental assays showed that the Fe3O4@SiO2@PIL can detect the concentration of CGA within 7 min, and has a good linear relationship with CGA in the concentration range of 0.025–2 μM (R2 = 0.9989) with a detection limit of 10 nM (S/N = 3). Moreover, the Fe3O4@SiO2@PIL exhibited excellent selectivity and can be reused for at least 5 runs, indicating its good stability and reusability. Finally, the Fe3O4@SiO2@PIL was used to selectively separate CGA in real fruit samples with the recovery ranging from 93.4% to 103.0% and the relative standard deviation (RSD) between 0.7% and 5.1%. This study gives a new insight into the utilization of magnetic materials by grafting boric acid functionalized ionic liquids for specific and rapid detection of natural cis-diol-containing compounds.
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APPLIED AND ENVIRONMENTAL MICROBIOLOGY
·
2022
·
IF 5.005
Qi Shen,Xiao-Ting Zhou,Qian Guo,Yu-Zhen Xue,Ya-Ping Xue,Yu-Guo Zheng
Pichia pastoris is widely used for the production of valuable recombinant proteins. An advantage of P. pastoris over other expression systems is that it secretes low levels of endogenous proteins, which facilitates the purification processes if the desired recombinant proteins are efficiently secreted into the culture medium. However, not all recombinant proteins can be successfully secreted by P. pastoris, especially enzymes that are located in intracellular compartments in their native hosts. Few studies have reported strategies for releasing recombinant proteins which cannot be secreted by standard protocols. Here, we investigated whether this challenge can be addressed using novel secretion leaders. Analysis of the secretome and transcriptome of P. pastoris indicated that the four genes with the highest protein-to-transcript ratios were EPX1, PAS_chr3_0030, SCW10, and UTH1, suggesting that their gene products contain efficient secretion leaders. Our data revealed that the signal peptide derived from the PAS_chr3_0030 gene product conferred secretion competence to certain industrial enzymes, e.g., a nitrilase of Alcaligenes faecalis ZJUTB10, a ribosylnicotinamide kinase of P. pastoris, and a glucose dehydrogenase of Exiguobacterium sibiricum. Therefore, the signal peptide derived from the PAS_chr3_0030 gene product represents a novel secretion sequence for the secretory expression of recombinant enzymes in P. pastoris.IMPORTANCE Although P. pastoris is widely used for the secretory production of pharmaceutical proteins, its successful applications in the secretory production of industrial enzymes are limited. The α-mating factor pre-pro leader is the most widely used secretion signal in P. pastoris, but numerous industrial enzymes cannot be secreted using it. The importance of this study is that we identified a signal peptide derived from the PAS_chr3_0030 gene product which conferred secretion competence to three-quarters of the enzymes tested. This signal peptide derived from the PAS_chr3_0030 gene product may facilitate the application of P. pastoris in industrial biocatalysis.
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ELECTROCHIMICA ACTA
·
2022
·
IF 7.336
Xiaohui Niu,Simeng Yan,Jinliang Chen,Hongxia Li,Kunjie Wang
Chiral metal-organic frameworks (MOF) have received extensive attention from researchers due to their chiral properties and potential applications in chiral-related fields. However, the construction of chiral metal-organic framework remains challenging due to the unpredictability of the synthesis process and the difficulty in keeping chirality during the growth of chiral MOF. Herein, a chiral MOF (D-His-ZIF-8) is reported for the construction of electrochemical sensing interface, which was synthesized via in-situ substitution of 2-methylimidazole on ZIF-8 by D-histidine (D-His). The introduction of Ketjen Black (KB) to the D-His-ZIF-8 sensing interface can improve its conductivity. The electrochemical recognition results show that KB/D-His-ZIF-8 has enantiodiscrimination ability for amino acids in voltammetry experiments. The best recognition efficiency is observed with Trp enantiomers . The recognition mechanism shows that the chiral nanochannel of D-His-ZIF-8 is conducive to the binding of L-amino acid, which will lead to the recognition of chiral molecules of different configurations. This research points to the possibility of developing further chiral recognition protocols based on D-His-ZIF-8, particularly with the suggested improvement in the preparation procedure of chiral MOF.
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Nature Communications
·
2021
·Vol. 12
·期 1
·1-12
·
IF 14.919
Xie Chao,Lin Longfei,Huang Liang,Wang Zixin,Jiang Zhiwei,Zhang Zehui,Han Buxing
Selective cleavage of C-C bonds is very important in organic chemistry, but remains challenging because of their inert chemical nature. Herein, we report that Zn/NC-X catalysts, in which Zn 2+ coordinate with N species on microporous N-doped carbon (NC) and X denotes the pyrolysis temperature, can effectively catalyze aerobic oxidative cleavage of C(CO)-C bonds and quantitatively convert acetophenone to methyl benzoate with a yield of 99% at 100 °C. The Zn/NC-950 can be applied for a wide scope of acetophenone derivatives as well as more challenging alkyl ketones. Detail mechanistic investigations reveal that the catalytic performance of Zn/NC-950 can be attributed to the coordination between Zn 2+ and N species to change the electronic state of the metal, synergetic effect of the Zn single sites with their surrounding N atoms, as well as the microporous structure with the high surface area and structural defects of the NC.
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INORGANIC CHEMISTRY
·
2024
·
IF 4.3
Mengyun Lu,Xinwen Jia,Wenjing Zhang,Wuduo Zhao,Ajuan Yu,Gangfeng Ouyang
The enantioselective performance of porous chiral metal–organic frameworks (CMOFs) is closely related to the pore size and uniformity of easily accessible active sites. The chiral recognition efficiency of microporous CMOFs is hindered by the restricted diffusion of the guest. Hierarchical porous chiral CMOFs with multiple pore size regimes ranging from micropores to macropores have emerged as potential candidates in chiral separation applications. 3DOM Zn-MOF-74 crystalline porous material with ordered macro–micropore structure was prepared with a general bottom-up strategy by carrying out the controllable confined growth of Zn-MOF-74 precursor in a removable three-dimensional ordered macroporous (3DOM) polystyrene (PS) template. Then l-tryptophan ( l -Trp) was introduced into MOFs by the strategy of postsynthetic modifications, and finally, a chiral hierarchical porous functional material 3DOM Zn-MOF-74-l-Trp was successfully fabricated. Based on the two luminescent centers from the achiral ligand H4DOBC and chiral ligand l-Trp, the proportional fluorescence sensor 3DOM Zn-MOF-74-l-Trp was hopeful to be applied in the field of enantioselective fluorescence sensing. The enantioselectivity factor values of microporous M-Zn-MOF-74-l-Trp for 1,1′-bi-2-naphthol (Binol) and mandelic acid (MA) were 1.08 and 1.12, respectively. In comparison, the construction of hierarchical porous structure greatly enhanced the chiral recognition performance, which may be due to the improved mass-transfer efficiency of chiral guest molecules and highly swelled accessibility to the chiral recognition sites in this CMOF composite, making the enantioselectivity factor values correspondingly increased to 1.29 and 2.26, respectively.
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JOURNAL OF PHYSICAL CHEMISTRY B
·
2024
·
IF 2.8
Qi Duan,Zhicheng Ye,Kangfu Zhou,Feifei Wang,Cheng Lian,Yazhuo Shang,Honglai Liu
Transdermal behavior is a critical aspect of studying delivery systems and evaluating the efficacy of cosmetics. However, existing methods face challenges such as lengthy experiments, high cost, and limited model accuracy. Therefore, developing accurate transdermal models is essential for formulation development and effectiveness assessment. In this study, we developed a multiscale model to describe the transdermal behavior of active ingredients in the stratum corneum. Molecular dynamics simulations were used to construct lipid bilayers and determine the diffusion coefficients of active ingredients in different regions of these bilayers. These diffusion coefficients were integrated into a multilayer lipid pathway model using finite element simulations. The simulation results were in close agreement with our experimental results for three active ingredients (mandelic acid (MAN), nicotinamide (NIC), and pyruvic acid (PYR)), demonstrating the effectiveness of our multiscale model. This research provides valuable insights for advancing transdermal delivery methods.
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ACS Nano
·
2025
·
IF 16
Jinglin Shen,Jing Fu,Paritosh Mahato,Minggan Wang,Baicheng Liu,Zhe Yang,Wei Qi,Di Sun,Xia Xin
The transformation of metal nanocluster (MNC)-based heterochiral assemblies into their homochiral analogues is a compelling goal inspired by the ubiquitous homochirality observed in living systems. Owing to the intricate factors governing nanomaterial chirality, the precise control of supramolecular chirality in MNCs remains rarely demonstrated. Herein, we demonstrated the coassembly behavior of AuNCs protected by 6-propyl-2-thiouracil (Au3PRT3) with chiral mandelic acid (MA), which revealed the formation of hybrid chiral superstructures of P- and M-helices in a single system. Combined experimental and theoretical studies comprehensively reveal that the enol-keto isomerization of the Au3PRT3 staple motif is primarily responsible for the emergence of P- and M-helices during coassembly. The negatively charged enol-type Au3PRT3 (Au3PRT3enol) interacts directly with S-MA molecules and forms parallel malposed dimers, resulting in the formation of P-helices. In contrast, the dissociation of H+ ions triggers enol-keto isomerization within the PRT ligand. The resulting keto-type isomer (Au3PRT3keto) then interacts with S-MA molecules, promoting vertical stacking of dimers that lead to the formation of M-helices. Based on this observation, the addition of S-MA molecules with the preformed Au3PRT3keto exclusively induces the formation of homochiral M-helices. In this way, the toggling of multiple chiral superstructures was achieved by leveraging facile Au3PRT3enol-Au3PRT3keto isomerization. This work elucidates the precise control of chiral structures by isomerization of surface motifs of AuNCs and presents a paradigm for investigating the structure–property relationship of AuNC materials. This approach offers a strategic pathway for constructing artificial supramolecular composite systems with diverse chiral architectures, potentially advancing our understanding of chirality evolution in natural systems and aiding its biomimetic replication.
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CRYSTAL GROWTH & DESIGN
·
2025
·
IF 3.4
Detao Li,Zichen Ning,Feiqiang He,Zhi Gao,Limin Zhou,Li Xu,Zhijian Zheng,Jerry Heng,Shichao Du,Jinbo Ouyang
To enable efficient separation of chiral drugs and enhance their practical utility, this study investigates cocrystallization as a novel separation and purification strategy. Using R/S-mandelic acid and d/l-prolinamide as model compounds, we screened potential cocrystal/salt coformers and successfully synthesized seven novel chiral salts. The proton transfer was elucidated by analyzing molecular electrostatic potential differences at the hydrogen-bonding sites. Moreover, the formation mechanism of salts was explored through structural analyses, such as Hirshfeld surface calculations, energy framework assessments, and crystal void analysis. Considering the distinct properties of various chiral salts, we conducted competitive cocrystallization experiments, establishing a complementary chiral pairing principle that provides a theoretical foundation for cocrystallization-based chiral resolution. Based on these findings, we developed multiple processes for the separation of R- and S-mandelic acid as well as l- and d-prolinamide, achieving product purities exceeding 80%, which strongly demonstrate the feasibility of cocrystallization separation technology for chiral resolution. This work not only introduces a groundbreaking approach to chiral separation but also highlights the vast potential of cocrystallization technology in pharmaceutical purification and beyond.
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