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学者姓名：徐春发
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Abstract ：
Glycosyl aryl sulfones exhibit diverse biological activities. Herein, we developed a copper-promoted coupling strategy using glycosyl sodium sulfinates and aryl iodides or bromides, enabling efficient synthesis of carbohydrate-based sulfone with broad functional group compatibility. This method offers a versatile approach for the late-stage modification of bioactive molecules.
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| GB/T 7714 | Wang, Linyitian , Guo, Huize , Luo, Jiaxin et al. Copper-promoted late-stage glycosylsulfonylation of aryl iodide and bromide to access glycosyl aryl sulfones [J]. | ORGANIC & BIOMOLECULAR CHEMISTRY , 2025 . |
| MLA | Wang, Linyitian et al. "Copper-promoted late-stage glycosylsulfonylation of aryl iodide and bromide to access glycosyl aryl sulfones" . | ORGANIC & BIOMOLECULAR CHEMISTRY (2025) . |
| APA | Wang, Linyitian , Guo, Huize , Luo, Jiaxin , Zhen, Wenxu , Wang, Shiping , Xie, Zailai et al. Copper-promoted late-stage glycosylsulfonylation of aryl iodide and bromide to access glycosyl aryl sulfones . | ORGANIC & BIOMOLECULAR CHEMISTRY , 2025 . |
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N-glycosides exhibit diverse biological and pharmacological activities, making their efficient synthesis crucial for both biological research and drug development. Traditional acid-promoted N-glycosylation methods, which rely on the formation of oxocarbenium intermediates, often face significant challenges. These methods are water-sensitive and typically require neighboring group participation to achieve high selectivity. Furthermore, they depend on acid activation, rendering them incompatible with alkyl amine. Additionally, low-nucleophilicity amides often need to be converted into their TMS-derivatives to enhance reactivity, limiting the direct use of such substrates. In contrast, radical-based strategies have emerged as a promising alternative, addressing many of these limitations and leading to notable advances in N-glycosylation. This review explores the unique properties of N-glycosides, the inherent challenges of traditional N-glycosylation techniques, and the transformative advantages offered by radical-based approaches. Specifically, it highlights recent advancements in radical-mediated N-glycosylation, including photoredox radical strategies, radical/ionic hybrid approaches, and metallaphotoredox catalysis, accompanied by a detailed discussion of the underlying mechanisms. Finally, the ongoing challenges and potential future directions of N-glycoside synthesis using radical strategies are presented.
Keyword ：
Glycosyl radical Glycosyl radical N-glycosides N-glycosides N-glycosylation N-glycosylation Photocatalysis Photocatalysis Radical reactions Radical reactions
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| GB/T 7714 | Xu, Chunfa , Zhang, Qinshuo , Yusupu, Yimuran . Radical Strategy Towards N-glycosides: Current Advances and Future Prospects [J]. | CHEMBIOCHEM , 2025 , 26 (5) . |
| MLA | Xu, Chunfa et al. "Radical Strategy Towards N-glycosides: Current Advances and Future Prospects" . | CHEMBIOCHEM 26 . 5 (2025) . |
| APA | Xu, Chunfa , Zhang, Qinshuo , Yusupu, Yimuran . Radical Strategy Towards N-glycosides: Current Advances and Future Prospects . | CHEMBIOCHEM , 2025 , 26 (5) . |
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A novel and efficient method for the stereoselective and stereodivergent synthesis of both unprotected and protected styryl C-glycosides through the reaction of sodium glycosyl sulfinate and hypervalent styryl iodine reagents is described. Using 2-bromo-9-fluorenone as a photocatalyst, C-styryl glycosides with an E configuration were selectively obtained. Furthermore, the introduction of a newly designed iridium-based catalyst enabled the selective formation of glycosides predominantly in the Z configuration. Mechanistic studies reveal the glycosyl radical is involved in the transformation.
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| GB/T 7714 | Ma, Jialu , Yan, Weitao , Chen, Xinyu et al. Photoinduced Diastereoselective and Stereodivergent Synthesis of C-Styryl Glycosides [J]. | ORGANIC LETTERS , 2025 , 27 (21) : 5458-5463 . |
| MLA | Ma, Jialu et al. "Photoinduced Diastereoselective and Stereodivergent Synthesis of C-Styryl Glycosides" . | ORGANIC LETTERS 27 . 21 (2025) : 5458-5463 . |
| APA | Ma, Jialu , Yan, Weitao , Chen, Xinyu , Zhen, Wenxu , Yu, Jin , Wang, Ruo et al. Photoinduced Diastereoselective and Stereodivergent Synthesis of C-Styryl Glycosides . | ORGANIC LETTERS , 2025 , 27 (21) , 5458-5463 . |
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Numerous methods have been developed for peptide synthesis due to their great potential in drug discovery. However, the technique for tryptophan-cysteine conjugation is still underexplored. Herein, we present a TMSBr-promoted ligation of tryptophan and cysteine under mild conditions by using a sulfonate-modified cysteine substrate. This protocol features a broad scope and high site selectivity and is applicable for synthesis of cyclic peptide. Preliminary mechanistic studies reveal that the reaction proceeds via a radical process.
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| GB/T 7714 | Lu, Qingqing , Wen, Hongyan , Zhang, Qinshuo et al. Mild Lewis-Acid-Promoted Cysteine-Tryptophan Conjugation Involving a Radical Process [J]. | ORGANIC LETTERS , 2025 , 27 (23) : 6192-6197 . |
| MLA | Lu, Qingqing et al. "Mild Lewis-Acid-Promoted Cysteine-Tryptophan Conjugation Involving a Radical Process" . | ORGANIC LETTERS 27 . 23 (2025) : 6192-6197 . |
| APA | Lu, Qingqing , Wen, Hongyan , Zhang, Qinshuo , Zhang, Zhou , Wang, Shiping , Wang, Ruo et al. Mild Lewis-Acid-Promoted Cysteine-Tryptophan Conjugation Involving a Radical Process . | ORGANIC LETTERS , 2025 , 27 (23) , 6192-6197 . |
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Cyclic peptides are highly valued in drug discovery due to their enhanced biological properties. Despite their potential, the construction of an S-alkynyl moiety in a cyclic peptide remains challenging due to limited synthetic strategies. Herein, we describe a copper-catalyzed alkynylation of thiosulfonate-based peptides, enabling efficient and selective synthesis of S-alkynylated cysteines and peptides. The adjustment of the amount of base could significantly increase the efficiency. This method features a broad substrate scope, operational simplicity and compatibility with complex peptide structures.
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| GB/T 7714 | Zhang, Zhou , Ying, Junjie , Lu, Qingqing et al. Cu-catalyzed alkynylation of thiosulfonate-based peptide: an efficient approach to S-alkynyl-containing cyclic peptides [J]. | ORGANIC CHEMISTRY FRONTIERS , 2025 , 12 (8) : 2752-2758 . |
| MLA | Zhang, Zhou et al. "Cu-catalyzed alkynylation of thiosulfonate-based peptide: an efficient approach to S-alkynyl-containing cyclic peptides" . | ORGANIC CHEMISTRY FRONTIERS 12 . 8 (2025) : 2752-2758 . |
| APA | Zhang, Zhou , Ying, Junjie , Lu, Qingqing , Zhang, Qinshuo , Xu, Chunfa . Cu-catalyzed alkynylation of thiosulfonate-based peptide: an efficient approach to S-alkynyl-containing cyclic peptides . | ORGANIC CHEMISTRY FRONTIERS , 2025 , 12 (8) , 2752-2758 . |
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Glycosyl sulfonamides have been identified as novel inhibitors of carbonic anhydrase, showing great potential for cancer treatment. However, previous approaches to synthesizing glycosyl sulfonamides require multi steps, resulting in low efficiency and being time-consuming. Herein, we disclose a reductive coupling strategy that enables the modular synthesis of glycosyl sulfonamide using readily accessible glycosyl sulfinates and feedstock chemical nitroarenes. This method allows for the construction of rarely reported N-aryl glycosyl sulfonamides and exhibits tolerance to a variety of functional groups.
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| GB/T 7714 | Zhen, Wenxu , Ma, Jialu , Ni, Zhaohui et al. Modular synthesis of glycosyl sulfonamide via reductive coupling of glycosyl sulfinate and nitroarene [J]. | NEW JOURNAL OF CHEMISTRY , 2025 , 49 (9) : 3416-3421 . |
| MLA | Zhen, Wenxu et al. "Modular synthesis of glycosyl sulfonamide via reductive coupling of glycosyl sulfinate and nitroarene" . | NEW JOURNAL OF CHEMISTRY 49 . 9 (2025) : 3416-3421 . |
| APA | Zhen, Wenxu , Ma, Jialu , Ni, Zhaohui , Luo, Jiaxin , Shen, Xiaomin , Xie, Yusheng et al. Modular synthesis of glycosyl sulfonamide via reductive coupling of glycosyl sulfinate and nitroarene . | NEW JOURNAL OF CHEMISTRY , 2025 , 49 (9) , 3416-3421 . |
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Glycosylseleno scaffolds exhibit wide-ranging applications in multidisciplinary fields, particularly in drug discovery and biophysical chemistry, where they serve as valuable tools for biomolecular structural analysis. However, efficient methods toward glycosylseleno scaffolds remain underexplored. Herein, we present the design of a novel class of bench-stable reagents, glycosylselenosulfonates, which uniquely integrate radical reactivity with electrophilic properties, thereby facilitating the straightforward incorporation of glycosylseleno moieties under mild reaction conditions. Upon photoirradiation, the radical addition of alkynes with glycosylselenosulfonates proceeds at an exceptionally fast rate, achieving completion in less than 1 min. Likewise, the functionalization of cysteine-containing molecules is achieved in a comparably short time frame, typically within 1 min in most instances. Additive experiments involving various amino acids confirm the robustness of these transformations, demonstrating consistently high efficiency across diverse reaction environments with negligible interference. Importantly, successful peptide and protein labeling in aqueous conditions highlights the method's potential for bioorthogonal applications. These findings collectively underscore the broad applicability and operational simplicity of glycosylselenosulfonates in developing rapid and efficient labeling techniques for biological and chemical research. This work not only advances synthetic methodologies for glycosylseleno scaffolds but also opens new avenues for functional studies of complex biological systems.
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| GB/T 7714 | Yan, Weitao , Liu, Wenchao , Zhang, Qinshuo et al. Photoactivatable Electrophilic Glycosylselenosulfonates for Ultrafast Modification of Alkynes and Thiols [J]. | ACS CENTRAL SCIENCE , 2025 , 11 (8) : 1400-1407 . |
| MLA | Yan, Weitao et al. "Photoactivatable Electrophilic Glycosylselenosulfonates for Ultrafast Modification of Alkynes and Thiols" . | ACS CENTRAL SCIENCE 11 . 8 (2025) : 1400-1407 . |
| APA | Yan, Weitao , Liu, Wenchao , Zhang, Qinshuo , Lin, Wentao , Liao, Yujie , Geng, Yiqun et al. Photoactivatable Electrophilic Glycosylselenosulfonates for Ultrafast Modification of Alkynes and Thiols . | ACS CENTRAL SCIENCE , 2025 , 11 (8) , 1400-1407 . |
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A noncovalent organocatalytic concerted addition of phenol to glycal is developed for the stereoselective and regioselective construction of biologically important phenolic 2-deoxyglycosides, featuring wide substrate tolerance. The method relies on an anion-bridged dual hydrogen bond interaction which is experimentally proved by Nuclear Magnetic Resonance (NMR), Ultraviolet and visible (UV-vis), and fluorescence analysis. Experimental evidence including kinetic analysis, Kinetic Isotope Effect (KIE) studies, linear free energy relationship, Hammett plot, and density functional theory (DFT) calculations is provided for a concerted mechanism where a high-energy oxocarbenium ion is not formed. In addition, the potential utility of this method is further demonstrated by the synthesis of biologically active glycosylated flavones. The benchmarking studies demonstrate significant advances in this newly developed method compared to previous approaches. A concerted addition of phenol to glycal promoted by anion-bridged dual hydrogen bond interaction is disclosed, featuring excellent stereoselectivity and broad substrate tolerance. The unprecedented concerted addition pathway is confirmed by kinetic analysis, KIE studies, Hammett plot and DFT calculation. The synthesis of biologically active glycosylated flavones and benchmarking studies demonstrate the significant advance of this method.image
Keyword ：
concerted addition concerted addition glycosylation glycosylation hydrogen bond hydrogen bond organocatalysis organocatalysis phenolic glycoside phenolic glycoside
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| GB/T 7714 | Jiao, Qinbo , Guo, Zhenbo , Zheng, Mingwen et al. Anion-Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal [J]. | ADVANCED SCIENCE , 2024 , 11 (11) . |
| MLA | Jiao, Qinbo et al. "Anion-Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal" . | ADVANCED SCIENCE 11 . 11 (2024) . |
| APA | Jiao, Qinbo , Guo, Zhenbo , Zheng, Mingwen , Lin, Wentao , Liao, Yujie , Yan, Weitao et al. Anion-Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal . | ADVANCED SCIENCE , 2024 , 11 (11) . |
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Glycosyl aryl sulfones have gained significant attention due to their diverse range of biological activities. However, a straightforward synthesis under mild conditions remains a challenging endeavor. This work presents the first transition-metal-free glycosyl sulfonation, employing a readily prepared sodium glycosyl sulfinate in conjunction with diaryliodonium salts. The method is compatible with various sugar substrates including unprotected sugar derivatives. Notably, the transfer of an aryl moiety in unsymmetric diaryl iodonium salts is chemoselectively achieved by utilizing an anisyl or TMP fragment as a dummy ligand. Preliminary mechanistic studies suggest that the reaction may proceed through an intramolecular SNAr process with a four-membered ring transition state. Transition-metal-free glycosyl sulfonation employing a readily prepared sodium glycosyl sulfinate in conjunction with diaryliodonium salts was reported, featuring wide tolerance with unprotected sugar substrates.
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| GB/T 7714 | Luo, Jiaxin , Chen, Xinyu , Ding, Wenyan et al. Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones [J]. | NEW JOURNAL OF CHEMISTRY , 2024 , 48 (10) : 4218-4223 . |
| MLA | Luo, Jiaxin et al. "Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones" . | NEW JOURNAL OF CHEMISTRY 48 . 10 (2024) : 4218-4223 . |
| APA | Luo, Jiaxin , Chen, Xinyu , Ding, Wenyan , Ma, Jialu , Ni, Zhaohui , Xie, Lihuang et al. Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones . | NEW JOURNAL OF CHEMISTRY , 2024 , 48 (10) , 4218-4223 . |
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Abstract ：
Correction for 'Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones' by Jiaxin Luo et al., New J. Chem., 2024, 48, 4218-4223, https://doi.org/10.1039/D3NJ05942A.
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| GB/T 7714 | Luo, Jiaxin , Chen, Xinyu , Ding, Wenyan et al. Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones (vol 48, pg 4218, 2024) [J]. | NEW JOURNAL OF CHEMISTRY , 2024 , 48 (15) : 7021-7021 . |
| MLA | Luo, Jiaxin et al. "Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones (vol 48, pg 4218, 2024)" . | NEW JOURNAL OF CHEMISTRY 48 . 15 (2024) : 7021-7021 . |
| APA | Luo, Jiaxin , Chen, Xinyu , Ding, Wenyan , Ma, Jialu , Ni, Zhaohui , Xie, Lihuang et al. Transition-metal-free glycosyl sulfonation of diaryliodonium salts with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones (vol 48, pg 4218, 2024) . | NEW JOURNAL OF CHEMISTRY , 2024 , 48 (15) , 7021-7021 . |
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