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Article ; Online: Thiolation of Terminal Alkynes with Thiuram Disulfide Reagents Using Water as the Hydrogen Source: Stereoselective Synthesis of (

Wang, Dan / Du, Jing / Lin, Wan-Li / Li, Yue-Sheng / Dong, Zhi-Bing

2023 Volume 88, Issue 24, Page(s) 16906–16914

Abstract: A stereoselective and environmentally friendly thiolation of terminal alkynes was reported. Thiuram disulfide reagents (tetramethylthiuram disulfide and tetraethylthiuram disulfide) that reacted with alkynes in dimethyl sulfoxide (DMSO)/ ... ...

Abstract	A stereoselective and environmentally friendly thiolation of terminal alkynes was reported. Thiuram disulfide reagents (tetramethylthiuram disulfide and tetraethylthiuram disulfide) that reacted with alkynes in dimethyl sulfoxide (DMSO)/H
Language	English
Publishing date	2023-11-29
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.3c01730
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Article: Synthesis of Unsaturated (Co)polyesters from Ring-Opening Copolymerization by Aluminum Bipyridine Bisphenolate Complexes with Improved Protonic Impurities Tolerance

Chen, Xiao-Lu / Wang, Bin / Pan, Li / Li, Yue-Sheng

Macromolecules. 2022 Apr. 19, v. 55, no. 9

2022

Abstract: Synthesis of unsaturated polyesters (UPES) via ring-opening copolymerization (ROCOP) of maleic anhydride (MAH) and epoxides still remains a great challenge, because the reported catalytic systems generally showed low catalytic activity or complete ... ...

Abstract	Synthesis of unsaturated polyesters (UPES) via ring-opening copolymerization (ROCOP) of maleic anhydride (MAH) and epoxides still remains a great challenge, because the reported catalytic systems generally showed low catalytic activity or complete deactivation at low catalyst concentration and exhibit poor tolerance to protonic impurities. In this work, we synthesized a series of bipyridine bisphenolate aluminum (BpyBph-Al) complexes and used these complexes to catalyze the MAH/epoxide copolymerization for synthesis of UPES. UPES with perfectly alternating structure could be synthesized using BpyBph-Al complexes without onium salt as cocatalyst, and the catalytic activities seem to be dependent on the steric and electronic effects of the ligands as well as the leaving ability of the axial group. The catalytic activities were further increased in the binary catalysts consisting of a BpyBph-Al as Lewis acid and an onium salt as a Lewis base. Compared with salen-Al/onium salt and typical Lewis pairs, the BpyBph-Al/onium salt binary system exhibited a completely maintained catalytic activity even when the [epoxide]/[MAH]/[catalyst pair] feed ratio was high up to 25 000:5000:1 ([catalyst pair] = 0.004 mol %). In addition, BpyBph-Al/onium salt exhibited better tolerance to protonic impurity than salen-Al/onium salt and Lewis pairs. The catalytic activity was slightly decreased (about 15%) in the presence of 100 equiv (relative to catalyst) of external-added maleic acid, while a substantial decrease in activity or complete deactivation was observed in the ROCOPs catalyzed by salen-Al/onium salt and Lewis pairs. These features of BpyBph-Al/onium salt further allowed UPES synthesis by using commercial MAH without any purification as a comonomer. The maleic acid residuals in the commercial MAH could serve as a chain transfer agent (CTA), and UPES polyols with uniform −OH chain ends were obtained via reversible-deactivation chain transfer reaction. Chain extension could be initiated by the active alkoxide end when adding the second cyclic anhydride after the full conversion of MAH, finally producing ABA-type triblock copolymers.
Keywords	Lewis acids ; Lewis bases ; aluminum ; catalysts ; catalytic activity ; composite polymers ; copolymerization ; epoxides ; ligands ; maleic acid ; maleic anhydrides ; polyols
Language	English
Dates of publication	2022-0419
Size	p. 3502-3512.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	1491942-4
ISSN	1520-5835 ; 0024-9297
ISSN (online)	1520-5835
ISSN	0024-9297
DOI	10.1021/acs.macromol.2c00034
Database	NAL-Catalogue (AGRICOLA)

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Article: One-Step Synthesis of Sequence-Controlled Polyester-block-Poly(ester-alt-thioester) by Chemoselective Multicomponent Polymerization

Chen, Xiao-Lu / Wang, Bin / Song, Dong-Po / Pan, Li / Li, Yue-Sheng

Macromolecules. 2022 Feb. 11, v. 55, no. 4

2022

Abstract: One-step chemoselective copolymerization of heterocyclic mixtures has been proved to be an efficient and straightforward approach to sequence-controlled (multi)block copolyesters compared with sequential addition and the macroinitiator method. However, ... ...

Abstract	One-step chemoselective copolymerization of heterocyclic mixtures has been proved to be an efficient and straightforward approach to sequence-controlled (multi)block copolyesters compared with sequential addition and the macroinitiator method. However, the scope of the monomer substrates is limited to the oxygenated heterocycles, and cyclic monomers containing other heteroatoms are underexplored. In this work, we extended the chemoselective polymerization to sulfur-containing heterocycles and successfully synthesized sequence-controlled block copolymers polyester-block-poly(ester-alt-thioester)s from anhydride/thioanhydride/epoxide monomers. This is realized via highly selective copolymerization of anhydride/epoxide prior to thioanhydride/epoxide copolymerization using rationally designed aluminum-based catalysts bearing bipyridine bisphenolate ligands. A significant difference between the reactivity of anhydride and thioanhydride with alkoxide chain end led to the excellent chemoselectivity. Moreover, transesterification side reactions are completely inhibited even at a high temperature up to 80 °C during the copolymerization, resulting in block copolymers with well-defined sequence structure on the polymer chains. Chemoselective copolymerization is also highly controlled in the use of a family of different epoxide derivatives, providing a powerful tool box for creating various advanced polythioesters for many different applications.
Keywords	anhydrides ; chemoselectivity ; composite polymers ; copolymerization ; heterocyclic compounds ; ligands ; polyesters ; temperature ; transesterification
Language	English
Dates of publication	2022-0211
Size	p. 1153-1164.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	1491942-4
ISSN	1520-5835 ; 0024-9297
ISSN (online)	1520-5835
ISSN	0024-9297
DOI	10.1021/acs.macromol.1c02303
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Article ; Online: Transcriptomes of Injured Lamprey Axon Tips: Single-Cell RNA-Seq Suggests Differential Involvement of MAPK Signaling Pathways in Axon Retraction and Regeneration after Spinal Cord Injury.

Jin, Li-Qing / Zhou, Yan / Li, Yue-Sheng / Zhang, Guixin / Hu, Jianli / Selzer, Michael E

Cells

2022 Volume 11, Issue 15

Abstract: Axotomy in the CNS activates retrograde signals that can trigger regeneration or cell death. Whether these outcomes use different injury signals is not known. Local protein synthesis in axon tips plays an important role in axon retraction and ... ...

Abstract	Axotomy in the CNS activates retrograde signals that can trigger regeneration or cell death. Whether these outcomes use different injury signals is not known. Local protein synthesis in axon tips plays an important role in axon retraction and regeneration. Microarray and RNA-seq studies on cultured mammalian embryonic or early postnatal peripheral neurons showed that axon growth cones contain hundreds to thousands of mRNAs. In the lamprey, identified reticulospinal neurons vary in the probability that their axons will regenerate after axotomy. The bad regenerators undergo early severe axon retraction and very delayed apoptosis. We micro-aspirated axoplasms from 10 growing, 9 static and 5 retracting axon tips of spinal cord transected lampreys and performed single-cell RNA-seq, analyzing the results bioinformatically. Genes were identified that were upregulated selectively in growing (
MeSH term(s)	Animals ; Axons/metabolism ; Lampreys/genetics ; Mammals ; Nerve Regeneration/genetics ; RNA-Seq ; Signal Transduction ; Spinal Cord Injuries/genetics ; Spinal Cord Injuries/metabolism ; Transcriptome/genetics
Language	English
Publishing date	2022-07-27
Publishing country	Switzerland
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ZDB-ID	2661518-6
ISSN	2073-4409 ; 2073-4409
ISSN (online)	2073-4409
ISSN	2073-4409
DOI	10.3390/cells11152320
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Article ; Online: Excellent Dark/Light Dual-Mode Photoresponsive Activities Based on g-C

Yang, Jin-Yu / Tang, Dong-Xu / Liu, Dong-Liang / Liu, Kun / Yang, Xiao-Jie / Li, Yue-Sheng / Liu, Yi

Molecules (Basel, Switzerland)

2023 Volume 28, Issue 22

Abstract: Photocatalytic technology for inactivating bacteria in water has received much attention. In this study, we reported a dark-light dual-mode sterilized g- ... ...

Abstract	Photocatalytic technology for inactivating bacteria in water has received much attention. In this study, we reported a dark-light dual-mode sterilized g-C
MeSH term(s)	Nanogels ; Escherichia coli ; Staphylococcus aureus ; Electrons ; Microscopy, Electron, Scanning
Chemical Substances	Nanogels
Language	English
Publishing date	2023-11-11
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules28227544
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Article ; Online: Artificial nonenzymatic antioxidant Prussian blue/KGM-BSA nanocomposite hydrogel dressing as ROS scavenging for diabetic wound healing.

Tang, Dong-Xu / Liu, Kun / Yang, Jin-Yu / Wang, Zhi-Jun / Fu, Li-Li / Yang, Xiao-Jie / Li, Yue-Sheng / Huang, Bin / Liu, Yi

International journal of biological macromolecules

2024 Volume 266, Issue Pt 1, Page(s) 131106

Abstract: The process of diabetic wound healing was influenced by the excessive proliferation of reactive oxygen species (ROS). Therefore, in the process of healing diabetic wounds, it was crucial to removing ROS. This study designed composited nanoparticles: KBP, ...

Abstract	The process of diabetic wound healing was influenced by the excessive proliferation of reactive oxygen species (ROS). Therefore, in the process of healing diabetic wounds, it was crucial to removing ROS. This study designed composited nanoparticles: KBP, consisted by Konjac glucomannan, bovine serum albumin, and Prussian blue. Then they were embedded in Konjac glucomannan and hydroxypropyl trimethylammonium chloride chitosan composite hydrogel (KH), The KBP@KH hydrogel finally achieved excellent efficacy in diabetic wound healing. The in vitro and in vivo experiments demonstrated that KPB nanoparticles exhibited favorable ROS scavenging capability and biosafety. The KBP@KH hydrogel not only effectively eliminated ROS from diabetic wounds, but also exhibited excellent wound adaptability. The KBP@KH hydrogel facilitated angiogenesis and suppressed the production of inflammatory factors. Overall, the KBP@KH hydrogel dressing was characterized by its user-friendly nature, safety, and high efficiency.
MeSH term(s)	Wound Healing/drug effects ; Animals ; Ferrocyanides/chemistry ; Ferrocyanides/pharmacology ; Nanocomposites/chemistry ; Reactive Oxygen Species/metabolism ; Serum Albumin, Bovine/chemistry ; Mannans/chemistry ; Mannans/pharmacology ; Hydrogels/chemistry ; Hydrogels/pharmacology ; Antioxidants/pharmacology ; Antioxidants/chemistry ; Diabetes Mellitus, Experimental/drug therapy ; Mice ; Bandages ; Rats ; Male ; Chitosan/chemistry ; Chitosan/analogs & derivatives ; Chitosan/pharmacology ; Free Radical Scavengers/pharmacology ; Free Radical Scavengers/chemistry ; Cattle ; Humans
Chemical Substances	Ferrocyanides ; ferric ferrocyanide (TLE294X33A) ; Reactive Oxygen Species ; Serum Albumin, Bovine (27432CM55Q) ; Mannans ; Hydrogels ; Antioxidants ; (1-6)-alpha-glucomannan (36W3E5TAMG) ; Chitosan (9012-76-4) ; Free Radical Scavengers
Language	English
Publishing date	2024-03-27
Publishing country	Netherlands
Document type	Journal Article ; Review
ZDB-ID	282732-3
ISSN	1879-0003 ; 0141-8130
ISSN (online)	1879-0003
ISSN	0141-8130
DOI	10.1016/j.ijbiomac.2024.131106
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Zs.B 2374: Show issues

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Article: Constructing ABA- and ABCBA-Type Multiblock Copolyesters with Structural Diversity by Organocatalytic Self-Switchable Copolymerization

Li, Chen / Dang, Yan-Feng / Wang, Bin / Pan, Li / Li, Yue-Sheng

Macromolecules. 2021 June 18, v. 54, no. 13

2021

Abstract: Self-switchable ring-opening copolymerization of epoxides, cyclic anhydrides, and cyclic esters catalyzed by an organocatalyst has been proved to be a promising approach to sequence-controlled (multi)block copolymers. However, the scope of the cyclic ... ...

Abstract	Self-switchable ring-opening copolymerization of epoxides, cyclic anhydrides, and cyclic esters catalyzed by an organocatalyst has been proved to be a promising approach to sequence-controlled (multi)block copolymers. However, the scope of the cyclic esters is only limited to lactide, and selection of some anhydrides usually produced random copolymers with an ill-defined sequence. To overcome these challenges, we investigated the one-pot selective polymerization of O-carboxyanhydrides (OCAs)/cyclic anhydrides/epoxides and established an alternative pathway for well-defined multiblock copolyesters with structural diversity and functionality. A potential organocatalyst for self-switchable copolymerization was optimized using ring-opening polymerization of OCA and ring-opening alternating copolymerization of cyclic anhydrides/epoxides as model reactions. Subsequently, the chemoselectivity in terpolymerization was investigated by kinetic studies, and the formation of the sequence-defined triblock copolymer was identified by NMR and GPC analysis. Density functional theory (DFT) calculations for model reactions were also conducted to illustrate the excellent chemoselectivity in terpolymerization. The newly established self-switchable pathway exhibited broad monomer adaptability, and the structures of the monomer (including some challenging anhydrides) have no effect on the chemoselectivity. Finally, one-step synthesis of ABCBA-type pentablock copolyester without external monomer addition was explored from a self-switchable quadri-polymerization of OCAs, cyclic anhydries, epoxides, and lactide.
Keywords	anhydrides ; catalytic activity ; chemoselectivity ; composite polymers ; copolymerization ; density functional theory ; epoxides ; organocatalysts ; polyesters
Language	English
Dates of publication	2021-0618
Size	p. 6171-6181.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	1491942-4
ISSN	1520-5835 ; 0024-9297
ISSN (online)	1520-5835
ISSN	0024-9297
DOI	10.1021/acs.macromol.1c00767
Database	NAL-Catalogue (AGRICOLA)

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Article: Alkali Metal Carboxylates: Simple and Versatile Initiators for Ring-Opening Alternating Copolymerization of Cyclic Anhydrides/Epoxides

Chen, Chong-Min / Xu, Xiaowei / Ji, He-Yuan / Wang, Bin / Pan, Li / Luo, Yi / Li, Yue-Sheng

Macromolecules. 2021 Jan. 07, v. 54, no. 2

2021

Abstract: In this contribution, we thoroughly investigated the ring-opening alternating copolymerization (ROAC) of cyclic anhydride and epoxide by using commercially available alkali metal carboxylates (AMCs) as the simple and green initiators. The idea of our ... ...

Abstract	In this contribution, we thoroughly investigated the ring-opening alternating copolymerization (ROAC) of cyclic anhydride and epoxide by using commercially available alkali metal carboxylates (AMCs) as the simple and green initiators. The idea of our work is based on the coordination effects of epoxide on an AMC and the formation of AMC–epoxide adducts, which will weaken the interaction between metal cation and its carboxylate counterion and therefore render the carboxylate to feasibly attack epoxides in a nucleophilic manner at high temperature. The coordination effects of epoxide on the AMC could be proved by Fourier transform infrared (FT-IR) spectroscopy and density functional theory (DFT) calculations. AMCs could effectively catalyze the copolymerization of phthalate anhydride (PA) and cyclohexene oxide (CHO) in bulk at 110 °C, affording polyesters with perfectly alternating structure. Potassium acetate (KOAc) was able to copolymerize some common cyclic anhydrides and epoxide, allowing for the preparation of polyesters with structural diversity. Of note, KOAc could mediate ROAC of PA with propylene oxide (PO) with a high molar feed ratio of [KOAc]/[PA]/[PO] = 1:20 000:150 000, affording poly(PA-alt-PO) with high molecular weight (>100 kDa). Finally, two different polymerization mechanisms, including anionic polymerization and cooperative catalysis, have been proposed according to the interaction strength between metal cation and carboxylate anion. In the “cooperative catalysis” mechanism, the alkali metal cation served as the Lewis acid to activate epoxide and cyclic active species were generated.
Keywords	Fourier transform infrared spectroscopy ; Lewis acids ; Lewis bases ; anhydrides ; catalytic activity ; copolymerization ; cyclohexenes ; density functional theory ; epoxides ; metal ions ; molecular weight ; phthalates ; potassium acetate ; propylene oxide ; temperature
Language	English
Dates of publication	2021-0107
Size	p. 713-724.
Publishing place	American Chemical Society
Document type	Article
Note	NAL-AP-2-clean
ZDB-ID	1491942-4
ISSN	1520-5835 ; 0024-9297
ISSN (online)	1520-5835
ISSN	0024-9297
DOI	10.1021/acs.macromol.0c02389
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Article: Cs₂CO₃-Promoted Hydrothiolation of Alkynes with Aryl Thioureas: Stereoselective Synthesis of (Z)-Vinyl Sulfides

Wang, Dan / Peng, Han-Ying / Yang, Meng-Meng / Hao, Er-jun / Li, Yue-Sheng / Dong, Zhi-Bing

Journal of organic chemistry. 2021 June 08, v. 86, no. 12

2021

Abstract: A metal-free Cs₂CO₃-promoted hydrothiolation of alkynes with aryl thioureas for stereoselective synthesis of (Z)-vinyl sulfides has been reported. Vinyl thioethers were obtained without a metal catalyst in good yields via anti-Markovnikov and cis ... ...

Abstract	A metal-free Cs₂CO₃-promoted hydrothiolation of alkynes with aryl thioureas for stereoselective synthesis of (Z)-vinyl sulfides has been reported. Vinyl thioethers were obtained without a metal catalyst in good yields via anti-Markovnikov and cis addition. The protocol features a broad substrate scope of the starting materials, high atom economy, good yields, and exclusive stereoselectivity, showing potential synthetic value for the synthesis of a diversity of (Z)-vinyl thioethers.
Keywords	alkynes ; catalysts ; organic chemistry ; stereoselective synthesis ; stereoselectivity
Language	English
Dates of publication	2021-0608
Size	p. 8457-8464.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.1c00309
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: One-Step Access to Sequence-Controlled Block Copolymers by Self-Switchable Organocatalytic Multicomponent Polymerization.

Ji, He-Yuan / Wang, Bin / Pan, Li / Li, Yue-Sheng

Angewandte Chemie (International ed. in English)

2018 Volume 57, Issue 51, Page(s) 16888–16892

Abstract: A one-step procedure for the self-switchable block copolymerization of monomer mixtures of epoxides, cyclic anhydrides, and lactide (LA) was developed by using simple organocatalysts without an external stimulus. This multicomponent polymerization ... ...

Abstract	A one-step procedure for the self-switchable block copolymerization of monomer mixtures of epoxides, cyclic anhydrides, and lactide (LA) was developed by using simple organocatalysts without an external stimulus. This multicomponent polymerization bridges two catalytic cycles involving ring-opening alternating copolymerization of epoxides with anhydrides and ring-opening polymerization (ROP) of LA, in which the presence/absence of anhydrides in mixed feedstocks switched the ROP of LA off/on. The self-switchable terpolymerization showed distinct noncoordinating and living nature, as well as perfect chemoselectivity. Different combinations of epoxides, anhydrides, and initiators enabled the generation of a variety of new block polyester polyols.
Language	English
Publishing date	2018-11-11
Publishing country	Germany
Document type	Journal Article
ZDB-ID	2011836-3
ISSN	1521-3773 ; 1433-7851
ISSN (online)	1521-3773
ISSN	1433-7851
DOI	10.1002/anie.201810083
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