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  • Qi Wu, Anyang Li, Ruibo He, Yaxi Wu, Lei Hou, Guoping Yang, Wenyan Zhang, Yao-Yu Wang
    Chinese Chemical Letters. 2024, 35(3): 108639-.

    Nitroaromatic hydrogenation catalysis without precious metals remains a longstanding challenge. The rate of electron transfer is the crucial factor affecting hydrogenation catalysis. Herein, an ionic Cd-based metal-organic framework (I-Cd-MOF) exhibiting a unique structure with one-dimensional (1D) opening nanochannels and good electron transfer ability was synthesized for catalyzing hydrogenation of 4-nitrophenol (4-NP). The catalytic activity of the unique I-Cd-MOF without noble metals is detected, which is higher than most reported noble metal catalysts. Remarkably, the reaction rate of I-Cd-MOF (4.28 min−1) is about 47.6 times higher than that of the Cd-based neutral MOF (N-Cd-MOF) with the similar crystalline structure. Liquid chromatograph mass spectrometer (LC-MS) and theoretical results demonstrate that 4-NP and five intermediates are stabilized in the channels of I-Cd-MOF, which increases the possibility of contact with H* and H2 generated at the Cd sites. The I-Cd-MOF was extended to other nitroaromatic hydrogenation catalysis, which still displays excellent activity. More importantly, the I-MOF@Filter membrane was successfully constructed for continuous hydrogenation catalytic reactions, which maintains a high catalytic performance after 7 cycles of recycling without washing. This work fills in the application of the I-MOFs in hydrogenation catalytic reactions and provides an effective way for the rapid and green degradation of nitroaromatic compounds.

  • Jin Huang, Jinwen Li, Rui Yan, Yuanyuan Qu, Fengzhen Guo, Lei Shen, Can-liang Ma, Jie Sun, Zhenjiang Li, Kai Guo
    Chinese Chemical Letters. 2024, 35(3): 108643-.

    The innovation in polymer design to rival conventional polyethylene glycol (PEG) is an important approach to achieving a more sustainable society. Here, cyclic PEG-like polycarbonates having high molecular weight (4.4–49.5 kg/mol) were enabled through zwitterionic ring-opening polymerization (ZROP) of macrocyclic carbonates (MCs) mediated by N-heterocyclic carbene (NHC). The thermodynamic behavior of polymerization depends on the ring size of monomers. During this process, the ZROP of 11-membered MC was driven by the change of enthalpy (ΔHp) which differed from the ZROP of 14-membered MC driven by the entropic change (ΔSp). Cyclic polycarbonates depicted improved thermostability (Td5% ≥ 204 ℃) and higher glass transition temperatures (Tg > ‒40 ℃) in comparison to their linear analogues (Td5% ≤ 185 ℃, Tg ~‒50 ℃). In addition, the mechanism of ZROP of MC was addressed through computational study. A distinct mechanism of polymerization distinguishable from the well-known NHC-mediated ZROP of cyclic esters was revealed, where the zwitterion from nucleophilic addition to MC, i.e. tetrahedral intermediate, cannot be ring-opened probably due to the delocalization of negative charge on the carbonate group, but serves as an active center for the polymerization. In comparison to PEG, the attained polymer demonstrated comparable hydrophilic and biocompatible properties, as revealed by the results of contact angle and in vitro cytotoxicity studies, suggesting that cyclic polycarbonate hold the promise as the alternative of PEG.

  • Yuntong Li, Hang Shi
    Chinese Chemical Letters. 2024, 35(3): 108650-.

    Mannich-type reactions are a widely used method for the synthesis of amines due to the readily availability of nucleophiles and electrophiles. However, the inclusion of alkylarenes instead of active carbon pronucleophiles such as aldehydes and ketones in these addition reactions has been a challenge due to the inherent difficulty of benzylic deprotonation. In this study, we present a novel approach for the construction of N-sulfonyl amines via rhodium-catalyzed addition of unbiased benzylic CH bonds to cyclic N-sulfonyl ketamines through π-coordination. This strategy enables the synthesis of a diverse range of N-sulfonyl amines, and subsequent diversification of the addition products showcases the synthetic potential of this protocol.

  • Yujie Zhang, Siyi Liu, Dongdong Chen, Xing Xu
    Chinese Chemical Letters. 2024, 35(3): 108666-.

    Fabrication of single atom catalysts (SACs) by a green and gentle method is important for their practical Fenton-like use. In this work, a high effective iron-based catalyst was prepared from the iron-rich Enteromorpha for NPX degradation via peroxymonosulfate (PMS). Both Fe-SACs and iron-clusters was fabricated from the intrinsic iron element in Enteromorpha after the urea saturation. The Fe-SACs/clusters can achieve 100% of NPX oxidation within 20 min with the kobs of 0.282 min−1. Quenching tests indicated that the radical pathways were not dominated in the catalytic systems, and strong electron transfer process can be induced in the Fe-SACs/clusters + PMS system by using the NPX as electron donor and Fe-SACs/clusters/PMS* complexes as electron acceptor. This result was consistent with the phenomenon observed in the galvanic oxidation system. In addition, the Fe-SACs/clusters was deposited onto the ceramic membrane (CM) by the spraying-crosslinking process to form a Fe-SACs/clusters@CM, which showed an effective and continuous NPX degradation in a heterogeneous PMS system.

  • Meijuan Zhou, Qian Liu, Mengting Pan, Ying Yang, Xiaoxia Dai, Changjun You
    Chinese Chemical Letters. 2024, 35(3): 108673-.

    N1-methyladenosine (m1A) is an important RNA modification that functions in various biological processes by interacting with cellular proteins. However, the binding proteins of N1-methyldeoxyadenosine (1mdA) in DNA remain largely unknown. Herein, we employed a quantitative proteomics strategy to identify the potential binding proteins of 1mdA in human cells. Our results revealed that serine‑threonine kinase receptor-associated protein (STRAP) can bind to 1mdA-carrying DNA. We further demonstrated that STRAP participates in alkylating agent-induced DNA damage response and can promote the repair of 1mdA embedded in DNA. Moreover, we investigated the effects of STRAP on 1mdA-induced perturbation in transcription using a shuttle vector- and next-generation sequencing-based assay, and found that STRAP is involved in the transcriptional bypass of 1mdA in human cells. Together, our study revealed STRAP as a novel 1mdA-binding protein in human cells and provided new insight into the biological implications of STRAP and 1mdA modification in human diseases.

  • Xingdong Yang, Shi-Ming Ying, Sen Zhang, Jinxia Dai, Wei Gao, Tian-Qi Wang, Jun-Qin Qiao, Hong-Zhen Lian, Li Mao
    Chinese Chemical Letters. 2024, 35(3): 108674-.

    Promethazine (PHZ) is used as a sedative in veterinary medicine, and its residue can threaten the health of human. The electrochemical detection of PHZ is suitable method for application in the field. However, the traditional electroanalysis is difficult to perform directly in meat samples due to matrix interference. This work integrates magnetic solid-phase extraction and differential pulse voltammetry for highly sensitive and selective determination of PHZ in beef and beef liver for the first time. CoFe2O4/graphene coated with C18-functionalized mesoporous silica (MG@mSiO2-C18) is synthesized as dispersed magnetic adsorbent to extract PHZ. Magnetic glassy carbon electrode modified with nitrogen-doped hollow carbon microspheres (HCM) attracts the MG@mSiO2-C18 with PHZ, and directly detects the PHZ without elution procedure. MG@mSiO2-C18 can separate PHZ to avoid the interference of impurities on following detection, and also concentrate PHZ on magnetic electrode. Additionally, the electrode modification with HCM can amplify the electrochemical signal of PHZ. Finally, the integrated PHZ determination method exhibits a wide linear range from 0.08 µmol/L to 300 µmol/L with a low limit of detection of 9.8 nmol/L. The beef sample analysis presents excellent recovery, demonstrating that this protocol is promising for the rapid and onsite detection of PHZ in real meat samples

  • Lan Zhou, Dongyang Wang, Chengbo Yang, Liang Deng
    Chinese Chemical Letters. 2024, 35(3): 108682-.

    Silyl cobalt species are putative intermediates in cobalt-catalyzed transformations of hydrosilanes. However, their reactivity has remained poorly understood. Reported here is the investigation on four-coordinate disilyl Co(Ⅱ) complexes with N-hetereocyclic carbene ligation. The reactions of [(ICy)2Co(vtms)] (ICy = 1, 3-dicyclohexylimidazol-2-ylidene, vtms = vinyltrimethylsilane) with primary and secondary hydrosilanes (3 equiv.) furnish the four-coordinate disilyl complexes [trans-(ICy)2Co(SiHRRʹ)2] (SiHRRʹ = SiH2Mes, 1; SiH2Ph, 2; SiH2Cy, 3; SiHPh2, 4; SiHEt2, 5) in moderate to good yields. The structures of 1, 2 and 4 were established by single-crystal X-ray diffraction. Solution magnetic susceptibility measurement and EPR spectroscopy indicate their low-spin nature (S = 1/2). Reactivity studies on 4 led to the establishment of the conversions of 4 to the disilyl dihydride Co(Ⅲ) complex [K(THF)][(ICy)2Co(H)2(SiHPh2)2]n (6) and the fluorosilyl Co(Ⅱ) complex [(ICy)2Co(THF)(SiFPh2)][BF4] (7) when 4 was treated with excess amount of K and AgBF4, respectively, in THF. These conversions hint at the high activity of low-valent and high-valent disilyl cobalt species [trans-(ICy)2Co(SiHPh2)2]1− and [trans-(ICy)2Co(SiHPh2)2]2+. Complex 4 is reactive toward terminal alkynes, but inert toward alkenes and internal alkynes. The reactions of 4 with terminal alkynes CyCCH and Me3SiCCH (3 equiv.) yield the Co(Ⅱ) complexes [(ICy)2Co(CCCy)2] (8) and [(ICy)2Co(CCSiMe3)((SiMe3)CCH2)] (9), respectively, along with H2SiPh2 and alkynylsilanes RCCSiHPh2 (R = Cy, SiMe3), whereas the reaction with 4-CF3C6H4CCH (3 equiv.) produce [(ICy)2Co(CCAr)((Ar)CCH(SiHPh2)CCHAr)] (Ar = 4-CF3C6H4) (10) and H2SiPh2. These reactions are proposed to involve σ-bond metathesis reactions between alkyne C(sp)-H bonds and Co-Si bonds in 4. Complexes 6–10 have been characterized by NMR spectroscopy, X-ray diffraction study, and elemental analysis.

  • Xuelei Deng, Meng Fan, Miao Wu, Xiaoyan Zhang, Ya Cheng, Jianye Xia, Yingping Zhuang, Weiping Zhu, Xuhong Qian, Yunpeng Bai
    Chinese Chemical Letters. 2024, 35(3): 108684-.

    A new continuous-flow process for the enzymatic synthesis of optically pure γ-lactones, which are used as flavors and fragrances in the food and cosmetic industries, was developed in a three-dimensional microfluidic reactor. The microchannels (175 mm in length, 0.9 mm in depth, and 1.72 mL in volume) were carved precisely inside a single borosilicate glass (90 mm × 75 mm × 12 mm) with ultrafast femtosecond laser micromachining. The flow field analysis and reaction simulation showed that the mixing of substrates and enzymes was enhanced, allowing the adjustment of residence time in a wide window. SmCRV4, a carbonyl reductase with excellent catalytic activity and enantioselectivity toward γ/δ-keto acids, was employed for the asymmetric synthesis of various chiral lactones. 30 mmol/L (R)-γ-decalactone (3g) can be obtained in 26 s with a space-time yield (STY) up to 16,877 g L−1 d−1, which is 14.4 times higher than the highest STY of batch reaction reported previously. This continuous-flow process was applied to the synthesis of 6 chiral lactones. In addition, the scaled-up synthesis of 3g was carried out in 6 cascade microreactors continuously for 6 h, demonstrating the feasibility and stability of the 3D continuous-flow process in enzymatic synthesis of optically pure compounds.

  • Lingpeng Zhan, Yanyi Huang, Guanbo Wang
    Chinese Chemical Letters. 2024, 35(3): 108685-.

    Matrix-assisted laser desorption/ionization (MALDI) mass spectrometry (MS) plays an indispensable role in analyzing protein covalent structures. The reliable identification of amino acid residues and modifications relies on the mass accuracy, which is highly dependent on calibration. However, the accuracy provided by the currently available calibrants still needs further improvement in terms of compatibility with multiple tandem MS modes or ion polarity modes, calibratable range, and minimizing suppression of and interference with analyte signals. Here aiming at developing a versatile calibrant to solve these problem, we designed a synthetic peptide format of calibrant R(GDP) (referred to as "Gly-Asp-Pro, GDP") according to the chemical natures of amino acids and polypeptide fragmentation rules in tandem MS. With four types of amino acid residues selected and arranged through rational designs, a GDP peptide produces highly regulated fragments that give rise to evenly spaced signals in each tandem MS mode and is compatible with both positive and negative ion modes. In internal calibration, its regulated fragmentation pattern minimizes interference with analyte signals, and using a single peptide as the input minimizes suppression of the analyte signals. As demonstrated by analyses of proteins including monoclonal antibody and Aβ-42, these features allowed significant increase of the mass accuracy and precision, which improved sequence coverage and sequence resolution in sequence analyses (including de novo sequencing). This rational design strategy may also inspire further development of synthetic calibrants that benefit structural analysis of biomolecules.

  • Ya-Nan Tang, Dingding Jiang, Xuejun Wang, Yunqi Liu, Dacheng Wei
    Chinese Chemical Letters. 2024, 35(3): 108688-.

    The outbreak of COVID-19 has drawn great attention around the world. SARS-CoV-2 is a highly infectious virus with occult transmission by many mutations and a long incubation period. In particular, the emergence of asymptomatic infections has made the epidemic even more severe. Therefore, early diagnosis and timely management of suspected cases are essential measures to control the spread of the virus. Developing simple, portable, and accurate diagnostic techniques for SARS-CoV-2 is the key to epidemic prevention. The advantages of point-of-care testing technology make it play an increasingly important role in viral detection and screening. This review summarizes the point-of-care testing platforms developed by nucleic acid detection, immunological detection, and nanomaterial-based biosensors detection. Furthermore, this paper provides a prospect for designing future highly accurate, cheap, and convenient SARS-CoV-2 diagnostic technology.

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