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Materials Advances · 2023 · IF 5

Cell surface functionalization with lysine ligand-containing copolymers for fibrinolytic activity

Shengjie Liu,Xingyu Heng,Wenjin Wang,Yang He,Wei Sun,Zhaoqiang Wu,Hong Chen

Although cell transplantation has achieved great success in the treatment of many intractable diseases, due to the effect of an instant blood-mediated inflammatory reaction (IBMIR), blood clots usually form on the surface of transplanted cells, resulting in a significant reduction in the survival of transplanted cells. Inspired by the fibrinolytic mechanism in human blood, this paper constructs lysine ligand-containing copolymer-functionalized cell surfaces for fibrinolytic activity. First, a copolymer (POLF) of oligoethylene glycol methacrylate (OEGMA), 6-amino-2-(2-methacylamido)-hexanoic acid (Lys) and fluorescein O-methacrylate (FluMA) was synthesized by reversible addition-fragmentation chain transfer (RAFT) copolymerization. Then, the copolymer POLF was modified onto the HeLa cell surface by codeposition with dopamine. An in vitro study showed that compared to unmodified HeLa cells, modified cells not only have good cell viability but can also resist fibrinogen adsorption and selectively bind plasminogen from plasma. More importantly, upon activation of plasminogen adsorbed to plasmin, the modified cells were able to rapidly lyse fibrin formed on their surface. This study offers a novel proof-of-concept for constructing transplanted cells with fibrinolytic activity.

CAS / MDL: 62-31-7 26915-72-0
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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2019 ·Vol. 411 ·期 18 ·4159-4166 · IF 3.286

Cleavable hydrophobic derivatization strategy for enrichment and identification of phosphorylated lysine peptides

Hu Yechen,Li Yang,Gao Hang,Jiang Bo,Zhang Xiaodan,Li Xiao,Wu Qiong,Liang Zhen,Zhang Lihua,Zhang Yukui

Because of structural flexibility and acid lability, the identification of phosphorylated lysine (pLys) peptides is a great challenge. We report here a cleavable hydrophobic derivatization (CHD) strategy for the enrichment and identification of pLys peptides. First, 2,5-dioxopyrrolidin-1-yl-3-(decyldisulfanyl)propanoate was synthesized to react with dephosphorylated lysine peptides, and then the derived peptides were captured by a C 18 column, followed by cleavage of the hydrophobic chain, with the specific label left on the target peptides for further identification. By CHD, the enrichment of pLys peptides from interfering peptides (1:1000 mass ratio) was achieved. Furthermore, CHD was applied to screen the pLys targets from Escherichia coli lysates, and 39 pLys sites from 35 proteins were identified. Gene Ontology (GO) analysis showed that these proteins played vital roles in catabolism, metabolism, biogenesis, and biosynthetic processes. All these results demonstrate that CHD might pave the way for comprehensive profiling of the pLys proteome.

研究领域: 生物化学 · 蛋白质组学
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Nature Communications · 2025 ·Vol. 16 ·期 1 ·1-13 · IF 15.7

The structural basis for the human procollagen lysine hydroxylation and dual-glycosylation

Peng Junjiang,Li Wenguo,Yao Deqiang,Xia Ying,Wang Qian,Cai Yan,Li Shaobai,Cao Mi,Shen Yafeng,Ma Peixiang,Liao Rijing,Zhao Jie,Qin An,Cao Yu

The proper assembly and maturation of collagens necessitate the orchestrated hydroxylation and glycosylation of multiple lysyl residues in procollagen chains. Dysfunctions in this multistep modification process can lead to severe collagen-associated diseases. To elucidate the coordination of lysyl processing activities, we determine the cryo-EM structures of the enzyme complex formed by LH3/PLOD3 and GLT25D1/ColGalT1, designated as the KOGG complex. Our structural analysis reveals a tetrameric complex comprising dimeric LH3/PLOD3s and GLT25D1/ColGalT1s, assembled with interactions involving the N-terminal loop of GLT25D1/ColGalT1 bridging another GLT25D1/ColGalT1 and LH3/PLOD3. We further elucidate the spatial configuration of the hydroxylase, galactosyltransferase, and glucosyltransferase sites within the KOGG complex, along with the key residues involved in substrate binding at these enzymatic sites. Intriguingly, we identify a high-order oligomeric pattern characterized by the formation of a fiber-like KOGG polymer assembled through the repetitive incorporation of KOGG tetramers as the biological unit.

CAS / MDL: 58-85-5
研究领域: 生物化学 · 结构生物学 · 医学遗传学
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CHEMISTRY-A EUROPEAN JOURNAL · 2023 · IF 4.3

Development of Lysine Crotonyl-mimic Probe to Covalently Identify H3K27Cr Interacting Proteins

Xiaochun Guo,Yuena Wang,Yuhao An,Zhihong Liu,Jianbo Liu,Jiaxin Chen,Mei-miao Zhan,Mingcha Liang,Zhanfeng Hou,Chuan Wan,Feng Yin,Rui Wang,Zigang Li

Histone lysine crotonylation (Kcr) is one newly discovered acylation modification and regulates numerous pathophysiological processes. The binding affinity between Kcr and its interacting proteins is generally weak, which makes it difficult to effectively identify Kcr-interacting partners. Changing the amide of crotonyl to an ester increased reactivity with proximal cysteines and retained specificity for Kcr antibody. We then designed the probe “H3g27Cr” by incorporating the ester functionality into a H3K27 peptide. Using this probe, we successfully identified multiple Kcr-interacting partners including STAT3, which had not reported previously. Further experiments suggested that STAT3 possibly could form complexes with Histone deacetylase HDACs to downregulate the acetylation and crotonylation of Histone H3K27. Our unique design provided intriguing tools to further explore Kcr-interacting proteins and elucidate their working mechanisms.

研究领域: 生物化学 · 分子生物学 · 表观遗传学
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CHEMICAL ENGINEERING JOURNAL · 2025 · IF 13.2

Controlled chain length production of ε-poly-l-lysine by Streptomyces albulus

Chenghao Fu,Wenjuan Dai,Aoxiang Liu,Yongxuan Liu,Qingshou Yao,Linghui Kong,Bo Yu,Xiuwen Wang,Jiayang Qin

ε-Poly- l -lysine (ε-PL), typically comprising 25–35  l -lysine residues, is a natural homopolymer with potent antibacterial properties. Its wider use is limited by two key challenges: precise control over peptide chain length and low production yields of low-molecular-weight (low-MW) ε-PL variants. In this study, we addressed these constraints by combining genetic engineering, carbon source modulation, and fermentation optimisation, enabling the targeted production of four well-characterised ε-PL variants. Multiple genetically engineered strains of Streptomyces albulus were developed and evaluated for ε-PL chain distribution. Particularly, S. albulus CICC-Pls880-LysP— co -overexpression of a mutated polylysine synthetase (Pls S880I) and a lysine importer (LysP)—produced ε-PL with chain lengths between 23 and 31 residues when grown in glucose-enriched fermentation broth and between 19 and 30 residues in glycerol-enriched broth. By contrast, the parental strain CICC-Pls-LysP yielded longer polymers (28–34 residues in glucose and 25–32 in glycerol), confirming the effectiveness of enzyme engineering in modulating chain length. Subsequent statistical optimisation of the fermentation medium, coupled with fed-batch cultivation strategies, enabled all four ε-PL variants (28–34, 25–32, 23–31, and 19–30 mer) to achieve production titres exceeding 50 g/L. Notably, supplementing l -lysine during fermentation significantly enhanced the yield of the low-MW variant (23–31 mer), reaching to 75.35 g/L. Antibacterial activity assays revealed a distinct correlation between chain length and efficacy, providing valuable insights into the structure–function relationships of ε-PL. This method, established for selectively synthesising ε-PL variants, overcomes historical yield bottlenecks for low-MW ε-PL, thereby broadening the applications of ε-PL.

CAS / MDL: 28211-04-3
研究领域: 生物技术 · 微生物发酵 · 合成生物学 · 高分子科学 · 应用微生物学
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ACS Sensors · 2025 · IF 9.1

Bioinspired Iontronic Gas Sensor for Selective CO2 Sensing via Reversible Lysine Carbamylation

Jiyuan Xue,Bingcheng Shen,Juan Wang,Juan Li,Hongran Zhao,Tong Zhang

Carbon dioxide (CO2) is ubiquitous in both natural and indoor atmospheres, playing a pivotal role in global climate regulation, air quality, and biological processes. However, their chemical inertness poses inherent challenges for developing compact, high-sensitivity detection platforms. In living organisms, CO2 often modulates protein function through reversible carbamylation of lysine residues, illustrating a finely tuned molecular recognition mechanism. Inspired by this principle, we developed a bioinspired iontronic sensor by embedding lysine moieties into a cross-linked poly(ethylene glycol) diacrylate (PEGDA) hydrogel. Upon exposure to CO2, the lysine ε-amino group forms transient carbamate adducts, inducing the electrostatic interaction, which disrupts Grotthuss-like conduction pathways and causes a distinct impedance increase. This lysine-based recognition enables high selectivity over interfering gases and operates reliably under ambient conditions. The resulting hydrogel sensor exhibits excellent linearity (R2 > 0.995) from 0 to 2000 ppm of CO2, with a theoretical detection limit of ∼76 ppm, suitable for indoor and ambient atmospheric CO2 monitoring at low concentrations. Furthermore, it maintains stable performance over at least 28 days of repeated measurements and shows negligible cross-sensitivity toward common interfering gases (e.g., H2S, CH4, and formaldehyde). By harnessing lysine–CO2 carbamylation within an ion-conducting matrix, our approach provides a versatile, low-power platform for precise CO2 sensing in applications ranging from indoor environmental evaluation to plant-level respiratory monitoring.

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ANALYST · 2011 ·Vol. 136 ·期 24 ·5302-5307 · IF 3.913

A novel silica based click lysine anion exchanger for ion exchange chromatography

Hongyue Guo,Changhu Chu,Yan Li,Bingcheng Yang,Xinmiao Liang

Ion chromatography (IC) is one of the most powerful analysis technologies for the determination of charged compounds. A novel click lysine stationary phase was prepared viaCu(I) catalyzed alkyne-azide 1,3-dipolar cycloaddition (CuAAC) and applied to the analysis of inorganic ions. The chromatographic evaluation demonstrated good performance (e.g. the plate number of thiocyanate is ∼50 000 plates m−1) and effective separation ability for the common inorganic anions with aqueous Na2SO4 eluent. The separation mechanism was observed to be mainly dominated by ion exchange interaction. The retention of these analytes is highly dependent on the pH value of eluent. Compared with the lysine stationary phase prepared via the conventional manner, the click lysine exchanger demonstrated shorter retention time and better ion separation characteristics under the same chromatographic conditions, which is a great advantage for rapid separation and analysis of inorganic ions.

研究领域: 分析化学 · 材料科学
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JOURNAL OF CHROMATOGRAPHY A · 2011 · IF 4.194

A novel click lysine zwitterionic stationary phase for hydrophilic interaction liquid chromatography

Hongyue Guo,Renhua Liu,Jinjin Yang,Bingcheng Yang,Xinmiao Liang,Changhu Chu

A novel type of zwitterionic HILIC stationary phase was prepared by covalently bonding the l -azido lysine on silica gel via click chemistry. The key intermediate azido lysine was synthesized by transformation the amino group in l -Boc-lysine to corresponding azido group and subsequent removal of the N-protected group (Boc). Finally, the azido lysine was covalently bonded to silica beads by click chemistry to get click lysine. Its structure was confirmed by FT-IR and elemental analysis. The new stationary phase showed good HILIC characteristics, when it was applied to separate polar and hydrophilic compounds, such as organic acids, cephalosporins and carbapenems. Compared with the commercial stationary phases, such as Atlantics HILIC and ZIC-HILIC, click lysine displayed better or similar chromatographic behaviors.

研究领域: 分析化学 · 生物化学
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TALANTA · 2018 · IF 4.244

Copper nanoclusters as probes for turn-on fluorescence sensing of L-lysine

Mingming Zhang,Juan Qiao,Shufeng Zhang,Li Qi

Herein, a unique protocol based on copper nanoclusters (CuNCs) probe for turn-on fluorescence sensing of L -lysine was developed. The fluorescent CuNCs with ovalbumin as the stabilizer was prepared by a simple, one-step and green method. When 370 nm was used as the excitation wavelength, the resultant CuNCs exhibited a pale blue fluorescence with the maximum emission at 440 nm. Interestingly, existence of L -lysine evoked the obvious fluorescence intensity increase of CuNCs. The detection limit of the proposed method for L -lysine was 5.5 μM, with a good linear range from 10.0 μM to 1.0 mM (r 2 = 0.999). Moreover, the possible mechanism for enhanced fluorescence intensity of CuNCs by addition of L -lysine was explored and discussed briefly. Further, the as-prepared fluorescent CuNCs was successfully applied in detection of L -lysine in urine. Our results demonstrated that L -lysine could be monitored by the probe, providing new path for construction of CuNCs as fluorescent probes and showing great potential in quantification of L -lysine in real samples.

研究领域: 分析化学 · 生物传感 · 医学检测
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JOURNAL OF POLYMER SCIENCE · 2021 ·Vol. 59 ·期 17 ·1958-1971 · IF 0

pH/enzyme/light triple-responsive vesicles from lysine-based amphiphilic diblock copolymers

Guoyang Qin,Cong Hu,Yanfen Jiang,Shuqi Dong,Li Liu,Hanying Zhao

We report the synthesis of pH- and enzyme-responsive amphiphilic diblock copolymers through reversible addition-fragmentation chain transfer polymerization of a lysine-derived methacrylate monomer comprising p -nitrobenzyl carbamate ( p NBC) functionality using a poly(ethylene glycol)-modified macro-chain transfer agent. Depending on the hydrophobic block length, the diblock copolymers self-assemble to form spherical micelles, wormlike micelles, and bilayered vesicles in the aqueous solution. The responsive behaviors of the polymeric vesicles to pH, enzyme, and light are investigated in detail. As the pH lowers to pH 5.0, the polymeric vesicles undergo a morphological transition from vesicles to spherical micelles. In the presence of nitroreductase and a cofactor NADH, the decomposition of p NBC releases the ε-NH 2 of the lysine moiety and hence induces the generation of the vesicles with crosslinked membranes at pH 7.4. Moreover, owing to the degradation of p NBC moiety under UV irradiation, the polymeric vesicles also demonstrate a photo-responsive feature. As the irradiation time prolongs, it is observed a light-triggered morphological transition from vesicles to wormlike micelles with network-like structures. Graphical

CAS / MDL: 13734-28-6
研究领域: 材料科学 · 生物化学 · 纳米医学
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Journal of Materials Chemistry B · 2022 ·Vol. 10 ·期 40 ·8274-8281 · IF 7.571

An antibacterial ε-poly-L-lysine-derived bioink for 3D bioprinting applications

Yahui He,Zheng Zhou,Yuting Huang,Wenxiang Zhu,Ning He,Xiaolong Zhu,Xiaoxiao Han,Hairong Liu

The limited availability of bioinks has hindered the application of 3D bioprinting to tissue engineering, and bacterial infection is a serious threat to these applications. Aiming to solve this problem, a novel ε-poly-L-lysine (EPL)-derived antibacterial bioink has been developed for 3D bioprinting and tissue-engineering applications. Three glycidyl methacrylate (GMA)-modified EPL products, EPLGMA-1, EPLGMA-2, and EPLGMA-3, were prepared by reacting 3, 4, and 5 mL GMA with 5 g EPL, respectively. EPLGMA-1, EPLGMA-2, and EPLGMA-3 were photocurable and their corresponding photo-crosslinked hydrogels, EPLGMA-1H, EPLGMA-2H, and EPLGMA-3H, all exhibited very high antibacterial rates, good biocompatibility, good degradability, and promising mechanical properties. After EPLGMA-1H, EPLGMA-2H, and EPLGMA-3H with encapsulated chondrocytes were incubated for 4 weeks, EPLGMA-3H was the best one among them for tissue-engineering applications due to its most efficient tissue regeneration. Carrying chondrocytes, the EPLGMA-3 solution was printed into hydrogel products with high-fidelity shapes and high cell viability using a projection-based 3D bioprinter. Following the implantation of chondrocyte-loaded EPLGMA-3H samples into nude mice for 4 weeks, cartilage-like tissue was regenerated, suggesting that EPLGMA-3 is a promising antibacterial bioink for 3D bioprinting and tissue-engineering applications.

CAS / MDL: 106-91-2
研究领域: 生物材料学 · 再生医学 · 组织工程
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Polymer Chemistry · 2014 ·Vol. 6 ·期 10 ·1758-1767 · IF 5.368

ε-Methacryloyl-L-lysine based polypeptides and their thiol–ene click functionalization

Qinghua Xu,Chaoliang He,Chunsheng Xiao,Shuangjiang Yu,Xuesi Chen

Facile synthesis of biopolymers that facilitate versatile post-polymerization modification is of great interest for biotechnological and biomedical applications. In this study, a methacryloyl-substituted L-lysine N-carboxyanhydride (LysMA-NCA) monomer was designed and synthesized, and methacryloyl-functionalized polypeptides were prepared through the ring opening polymerization (ROP) of the L-lysine-based monomer. The post-polymerization functionalization of the methacryloyl-containing polypeptides with various thiol-containing molecules was achieved with high efficiency through facile radical-mediated thiol–ene chemistry. Moreover, a block copolypeptide bearing both methacryloyl and alkynyl pendants was developed through successive ROP of LysMA-NCA and γ-propargyl-L-glutamate (PPLG-NCA). The sequential modification of the block copolypeptide with hydrophilic and hydrophobic molecules, respectively, was achieved by the successive alkyne–azido and thiol–ene “click” reactions. Overall, the facile synthesis of polypeptides bearing functional substituents and their versatile post-polymerization modification may serve as a useful platform for the development of various functional polymers.

CAS / MDL: 100-53-8
研究领域: 生物材料学 · 高分子化学 · 生物医学工程
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