Yufen Zhao’s research while affiliated with Ningbo University and other places

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Publications (774)


Our designs. A) Synthesis of N‐sulfonyl imidazoliums. B) Synthesis of amides, carboxylic esters, and carboxylic thioesters. C) Synthesis of phosphamides and phosphates. D) Synthesis of glucosides. E) Synthesis of sulfonamides and sulfonates.
Synthesis of N‐sulfonyl ammoniums. A) Reaction conditions: substituted imidazole (1), pyridine (1′) or DBU (5 mmol), sulfonic anhydride (2) or sulfonyl chloride (2′) (6 mmol), CH2Cl2 [2 in subscript] (10 mL), reaction for 5 minutes at 0 °C, then reaction for 30–60 minutes at room temperature (~25 °C). B) Reaction conditions: 1‐methylimidazole (1a) (50 mmol), trifluoromethanesulphonic anhydride (2a) (60 mmol), CH2Cl2 (100 mL), reaction for 10 minutes at 0 °C, then reaction for 50 minutes at room temperature (~25 °C).
N‐Sulfonyl imidazolium‐mediated amide bond formation between carboxylic acids and amines. A) Reaction conditions: carboxylic acid (4) (0.40 mmol), amine (5) (0.48 mmol), MIM‐Tf (3a) (0.48 mmol), 1‐methylimidazole (0.40 mmol) and CH2Cl2 (10 ml). Reaction at 0 °C for 5 minutes, and then reaction at room temperature (∼25 °C) for 10−60 minutes. Isolated yield. aUsing EIM‐Tf (3b) (0.48 mmol) and 1‐ethylimidazole (1b) (0.40 mmol) as the coupling reagent and base. bUsing DMIM‐Tf (3d) (0.48 mmol) and 1,2‐dimethylimidazole (1d) (0.40 mmol) as the coupling reagent and base. B) One‐pot two‐step synthesis of 13a.
N‐Sulfonyl imidazolium‐mediated dipeptide synthesis. A) Reaction conditions: acid partner (4) (0.2 mmol), amine partner (8) (0.24 mmol), MIM‐Tf (3a) (0.24 mmol), 1‐methylimidazole (1a) (0.44 mmol) and CH2Cl2 (5 ml). Reaction at 0 °C for 5 minutes, and then reaction at room temperature (∼25 °C) for 10−30 minutes. Isolated yield. The dr values were determined by chiral HPLC analysis. aUsing EIM‐Tf (3b) (0.24 mmol) and 1‐ethylimidazole (1b) (0.20 mmol) as the coupling reagent and base. bUsing DMIM‐Tf (3d) (0.24 mmol) and 1,2‐dimethylimidazole (1d) (0.20 mmol) as the coupling reagent and base. B) Gram‐scale synthesis of 13am.
Solid phase synthesis of polypeptide A.

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N‐Sulfonyl Imidazoliums as the Versatile Coupling Reagents and Sulfonating Reagents in Synthesis of Amides, Esters, Thioesters, Phosphoramides, Phosphoesters, Glycosides, Sulfonamides, and Sulfonates
  • Article
  • Publisher preview available

May 2025

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9 Reads

Hongyun Li

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Yue Zhang

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Here, we report a novel strategy for the first time: bench‐stable N‐sulfonyl imidazoliums were used as the robust and versatile coupling reagents and sulfonating reagents. Fast reactions of N‐sulfonyl imidazoliums with carboxylic acids or phosphodiesters formed carboxylic acid‐sulfonic acid mixed anhydrides and phospho‐sulfonic acid mixed anhydrides, respectively, and the subsequent treatments of the highly active intermediates with the corresponding nucleophilic partners in the presence of imidazoles at room temperature provided amides, dipeptides, carboxylic esters, carboxylic thioesters (almost without racemization during the formation of amides, dipeptides, esters, thioesters), phosphamides, and phosphoesters in high to excellent yields. This kind of N‐sulfonyl imidazolium as the coupling reagent was successfully applied in solid phase synthesis of a polypeptide containing 32 amino acid residues. This strategy was effectively extended to the construction of glycosides, and high steroselectivity and good yields were provided. In addition, reactions of N‐sulfonyl imidazoliums with amines or alcohols afforded the corresponding sulfonamides and sulfonates in excellent yields. This study should provide a highly efficient, economical, and practical strategy for construction of diverse molecules.

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McsB regulates CtsR thermosensing through periphery arginine phosphorylation

December 2024

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22 Reads

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1 Citation

Post-translational protein modifications (PTMs) are a ubiquitous phenomenon that exists in all domains of life. The bacterial transcription repressor CtsR becomes phosphorylated by the arginine kinase McsB when cells sense an elevated temperature in the environment. Here, we perform single-molecule experiments based on the protein-induced fluorescence enhancement (PIFE) effect to monitor the DNA-CtsR-McsB interaction. Our single-molecule analysis reveals that CtsR binds rapidly and stably to the cognate DNA and McsB transiently interacts with the DNA-bound CtsR. We determined the binding kinetics between McsB and the DNA-bound CtsR by single-molecule real-time binding assays, with kon and koff of 0.80 uM-1 s-1 and 0.14 s-1, respectively. Through this interaction, McsB does not remove CtsR from the DNA, but instead alters its thermosensing behavior, lowering the temperature threshold for CtsR dissociation. Phosphorylation of several periphery arginine residues on CtsR underlies a plausible molecular mechanism for this effect. Taken together, these results provide insights into how CtsR might integrate inputs from different environment stresses and regulate the initiation of the heat-shock response when cells are faced with complex environment conditions.


Citations (49)


... Therefore, systems based on the analyte-driven aggregation of AuNPs have been utilized for the colorimetric sensing of specific analytes through detection reporters on the AuNPs [32][33][34][35][36][37][38][39]. Notably, the ability of a single sensor to simultaneously detect multiple analytes has recently gained significant attention, owing to advantages including cost reduction and improved analytical efficiency [40][41][42][43][44]. Consequently, the design and synthesis of colorimetric sensors exhibiting high selectivity and sensitivity toward MOX, CIP, and Cr(III) have attracted increasing attention [45][46][47]. ...

Reference:

An Ultra-Sensitive Colorimetric Sensing Platform for Simultaneous Detection of Moxifloxacin/Ciprofloxacin and Cr(III) Ions Based on Ammonium Thioglycolate Functionalized Gold Nanoparticles
Advances in dual-function bioprobes for simultaneous detection of transition metal ions (Fe, Cu, Zn) and bioactive species
  • Citing Article
  • March 2025

Coordination Chemistry Reviews

... Some gram-negative bacteria, specifically those from the phylum Proteobacteria in which E. coli is classed, possess homologues of McsA and McsB [42]. Moreover, McsB was recently reported to bind in transient to the CtsR-DNA complex [43]. Therefore, if the role of McsB in E. coli and S. aureus are similar, it may be plausible that the entire McsB-CtsR (or equivalent E. coli repressor)-DNA-MMV1634391 complex was stabilised in the endogenous environment. ...

McsB regulates CtsR thermosensing through periphery arginine phosphorylation
  • Citing Preprint
  • December 2024

... These compounds have gained significant attention in the field of medicinal chemistry, where they exhibit activities such as antimicrobial, antiviral, antidiabetic, antioxidants and anticancer activity [1,2]. The structural framework of benzimidazole provides a versatile scaffold for the synthesis of novel compounds, which are capable of interacting with various biological targets due to their heteroatom-rich nature and ability to participate in hydrogen bonding and π-π stacking interactions [3,4]. ...

Structural insight into imidazopyridines and benzimidazoles: the importance of the hydrogen bond, π-stacking interactions and intramolecular charge transfer effect for fluorescence
  • Citing Article
  • January 2024

CrystEngComm

... Infrared spectroscopy of inner and outer layers of the travertine sample reveals three principal absorption features for calcite between 400 and 4000 cm −1 (Figure 4a). The antisymmetric stretching mode (ν 3 ) of the carbonate ion (CO 3 2− ) produces a prominent band at 1420 cm −1 , while outof-plane bending (ν 2 ) and in-plane bending (ν 4 ) appear at 872 and 709 cm −1 , respectively. These bands' shift is influenced depending on how each carbonate C−O bond interacts with infrared radiation. ...

Local pH variability scenario: Prebiotic synthesis of cyclic dipeptides via prolinamide on the Hadean Earth
  • Citing Article
  • July 2024

Palaeogeography Palaeoclimatology Palaeoecology

... In 2024, Wang et al. [62] reported an electrochemical method for the synthesis of phosphorylated indoles in the presence of Cp 2 Fe as the mediator under mild reaction conditions without the need for external oxidants. This method improves the scalability of the resulting products, which also exhibit enhanced anticancer activity. ...

Electrochemical Synthesis of Phosphorylated Indoles and Trp-Containing Oligopeptides
  • Citing Article
  • May 2024

Organic Letters

... Detailed descriptions of deep learning models for other PTM types are provided in supplementary materials (Section 1) due to space limitations [10]. ...

Nphos: Database and Predictor of Protein N -phosphorylation
  • Citing Article
  • April 2024

Genomics Proteomics & Bioinformatics

... Necroptosis is classified as a kind of programmed necrosis, which is manifested as resultant cell leakage following cell swelling and subsequent plasma membrane disruption, thereby provoking the immune system and strongly incurring proinflammatory effects (Shi et al. 2024). Necroptosis is involved in secondary brain injury subsequent to traumatic brain injury, ischemic stroke, ICH, and subarachnoid hemorrhage (L. ...

Protein phosphorylation and kinases: Potential therapeutic targets in necroptosis
  • Citing Article
  • March 2024

European Journal of Pharmacology

... Organophosphorus compounds are vital in various applications spanning organic synthesis, agrochemicals, pharmaceuticals, and innovative materials. [1][2][3][4][5][6][7][8] Among them, vinylated phosphorus compounds are of significant relevance in the pharmaceutical industry due to their potential to synthesize pharmacologically important and biologically active molecules, such as antibiotics and enzyme inhibitors. Furthermore, alkenyl phosphine oxides are recognized for their utility as monomers in polymer and materials science, emphasizing the extensive and critical role of phosphorus in advancing diverse scientific fields. ...

NaOAc-Assisted Aerobic Oxidation Protocol for the Synthesis of Pentacoordinate Chalcogenyl Spirophosphoranes with P-Se/P-S Bonds under Open Air
  • Citing Article
  • February 2024

The Journal of Organic Chemistry

... SCHEME 9 | N-to C-solution-phase synthesis using ynamide activation. prepared under so claimed "prebiotic conditions" in which Nacetamido amides were heated with amino amides in 0.5 M NaOH at 80 °C [58]. Moreover, peptides have been synthesized by ring-opening of N-alkyl N-Boc-diketopiperazines without epimerization on heating with amino esters in the neat and with peptide esters in toluene with a benzoic acid catalyst [59]. ...

A model for N-to-C direction in prebiotic peptide synthesis

Chemical Communications

... The cyclization occurred between 2-pyridinemethylamine and various aromatic aldehydes. This was a straightforward approach in which I 2 /H 2 O 2 worked as medium and afforded excellent yields in the range of 65%-98% (Scheme 32)[37].The proposed mechanism started with the reaction of H 2 O 2 and I 2 , also H 2 O 2 oxidized benzaldehyde to benzoic acid. Again, in the presence of I 2 , pyridine methylamine attacked benzaldehyde and formed an intermediate iminium ion 91, which changes to intermediate 92 with intramolecular attack of N-atom of pyridine. ...

I 2 /H 2 O 2 mediated synthesis and photophysical properties of imidazole-fused heterocycles via [4+1] cyclization approach