BioReagent, ≥98% BioReagent for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C Ships Wet ice Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 36 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
| Sonrisas canónicas | N[C@@H](CCC(=O)N[C@@H](CSSC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O |
|---|---|
| IUPAC Name | (2S)-2-amino-5-[[(2R)-3-[[(2R)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]-3-(carboxymethylamino)-3-oxopropyl]disulfanyl]-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid |
| InChIKey | YPZRWBKMTBYPTK-BJDJZHNGSA-N |
| INCHI | 1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1 |
| Isómeros SMILES | C(CC(=O)N[C@@H](CSSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)C(=O)NCC(=O)O)[C@@H](C(=O)O)N |
| WGK Alemania | 2 |
| RTECS | MC0556500 |
| Peso molecular | 612.63 |
| Beilstein | 1718700 |
| Reaxy-Rn | 1718700 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1718700&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Clase | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Peptides |
| Alternative Parents | Tetracarboxylic acids and derivatives N-acyl-alpha amino acids L-alpha-amino acids Dialkyldisulfides Amino acids Sulfenyl compounds Propargyl-type 1,3-dipolar organic compounds Carboxylic acids Carboximidic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Alpha peptide - N-acyl-alpha-amino acid - N-acyl-alpha amino acid or derivatives - Tetracarboxylic acid or derivatives - Alpha-amino acid - Alpha-amino acid or derivatives - L-alpha-amino acid - Amino acid or derivatives - Amino acid - Dialkyldisulfide - Organic disulfide - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Sulfenyl compound - Amine - Hydrocarbon derivative - Organic oxide - Primary aliphatic amine - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Organopnictogen compound - Primary amine - Carbonyl group - Aliphatic acyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. |
| External Descriptors | organic disulfide - glutathione derivative |
| Solubilidad | H 2 O: 0.1 M at 20 °C, clear, colorless |
|---|---|
| Rotación específica [α] | -105 ° (C=2, H2O) |
| Punto de fusión (°C) | 178°C |
| Peso molecular | 612.600 g/mol |
| XLogP3 | -9.100 |
| Hydrogen Bond Donor Count | 10 |
| Hydrogen Bond Acceptor Count | 16 |
| Rotatable Bond Count | 21 |
| Exact Mass | 612.152 Da |
| Monoisotopic Mass | 612.152 Da |
| Topological Polar Surface Area | 368.000 Ų |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Complexity | 879.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
| 1. Xiaoyu Yang, Shunbi Xie, Runzi Zhang, Yao Liu, Weifen Wu, Yi He. (2024) An efficient SERS detection platform based on roseate petal homochiral nanogold (Au RHNs) as substrate for sensitive detection of plastics in environmental water samples. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, [PMID:39721488] [10.1016/j.saa.2024.125642] |
| 2. Yamin Liu, Xunjiang Wang, Jiaojiao Wei, Kangning Fu, Yilin Chen, Linnan Li, Zhengtao Wang, Li Yang. (2024) Comprehensive Profiling of Amino Acids and Derivatives in Biological Samples: A Robust UHPLC-MS/MS Method for Investigating Acute Lung Injury. JOURNAL OF CHROMATOGRAPHY A, [PMID:38537486] [10.1016/j.chroma.2024.464816] |
| 3. Zhanqiu Tang, Xinyi Feng, Hongyuan Tian, Junhua Wang, Weidong Qin. (2024) Integration of glutathione disulfide-mediated extraction and capillary electrophoresis for determination of Cd(II) and Pb(II) in edible oils. FOOD CHEMISTRY, [PMID:38901338] [10.1016/j.foodchem.2024.140146] |
| 4. Jianwen Fei, Wei Yang, Yin Dai, Wei Xu, Huizhu Fan, Yani Zheng, Junli Hong, Jun Zhang, Wanying Zhu, Xuemin Zhou. (2024) Oxygen-functionalized Fe3O4@o-polypyrrole acting as high-efficiency oxidase mimics and their application in glutathione colorimetric sensing. TALANTA, [PMID:38943764] [10.1016/j.talanta.2024.126431] |
| 5. Jian Sun, Xiangxiang Zhang, Liu Xue, Liang Cheng, Jing Zhang, Xin Chen, Zhirong Shen, Kang Li, Lai Wang, Chichi Huang, Jing Song. (2024) Structural insights into the unique pH-responsive characteristics of the anti-TIGIT therapeutic antibody Ociperlimab. STRUCTURE, [PMID:38460520] [10.1016/j.str.2024.02.009] |
| 6. SunHongzheng , HanLongsen , GuoYueshuai , AnHuiqing , WangBing , ZhangXiangzheng , LiJiashuo , JiangYingtong , WangYue , SunGuangyi , ZhuShuai , TangShoubin , GeJuan , ChenMinjian , GuoXuejiang , WangQiang. (2024) The global phosphorylation landscape of mouse oocytes during meiotic maturation. EMBO JOURNAL, [PMID:39256562] [10.1038/s44318-024-00222-1] |
| 7. Jia Lin, Guoqing Yue, Kang Xiao, Deqing Yang, Xuxing Hao, Minlin Zheng, Pumo Cai, Qing'e Ji. (2023) Effects of low-concentration spinetoram wax-based bait stations on Bactrocera dorsalis (Diptera: Tephritidae). PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, [PMID:38072558] [10.1016/j.pestbp.2023.105705] |
| 8. Chen Na, Du Na, Shen Ruichen, He Tianpei, Xi Jing, Tan Jie, Bian Guangkai, Yang Yanbing, Liu Tiangang, Tan Weihong, Yu Lilei, Yuan Quan. (2023) Redox signaling-driven modulation of microbial biosynthesis and biocatalysis. Nature Communications, 14 (1): (1-13). [PMID:37884498] [10.1038/s41467-023-42561-3] |
| 9. Xiaofang Wang, Huiming Wang, Meining Zhang. (2023) A multi-stimuli-responsive nanochannel inspired by biological disulfide bond. TALANTA, [PMID:37348351] [10.1016/j.talanta.2023.124785] |
| 10. Luo Gu, Qiuyu Zhu, Xiaoyu Zou, Ru Song. (2023) Antibacterial Effect of Shrimp By-Products Hydrolysate on Specific Spoilage Organisms of Squid. MOLECULES, 28 (10): (4105). [PMID:37241846] [10.3390/molecules28104105] |
| 11. Jia Kong, Jinyao Hu, Jia Li, Jiaxing Zhang, Yuhe Shen, Tianli Yue, Xihui Shen, Yuefei Wang, Zhonghong Li, Yinqiang Xia. (2023) Rethreading Design of Ratiometric roGFP2 Mimetic Peptide for Hydrogen Peroxide Sensing. ANALYTICAL CHEMISTRY, [PMID:37161261] [10.1021/acs.analchem.3c00486] |
| 12. Yuwei Du, Lei Cao, Xinlu Li, Tongtong Zhu, Ruhong Yan, Wen-Fei Dong, Li Li. (2023) Preparation and application of high-brightness red carbon quantum dots for pH and oxidized L-glutathione dual response. ANALYST, 148 (10): (2375-2386). [PMID:37129055] [10.1039/D3AN00383C] |
| 13. Mengfei Liu, Hong Mo, Qingyu Gao, Ling Yuan. (2021) The pH dependence of emulsifying properties for glutathione disulfide at oil-water interfaces. BIOPHYSICAL CHEMISTRY, [PMID:34959125] [10.1016/j.bpc.2021.106748] |
| 14. Xiang-Rong Cheng, Piao-Han Tu, Wen-Le Dong, Bu-Tao Yu, Shu-Fang Xia, Mitchell N. Muskat, Bin Guan. (2021) Electrophilic thymol isobutyrate from Inula nervosa Wall. (Xiaoheiyao) ameliorates steatosis in HepG2 cells via Nrf2 activation. Journal of Functional Foods, [PMID:] [10.1016/j.jff.2021.104895] |
| 15. Qianqian Zhang, Junhua Wang, Zhao Meng, Rui Ling, Hang Ren, Weidong Qin, Zhenglong Wu, Na Shao. (2021) Glutathione Disulfide as a Reducing, Capping, and Mass-Separating Agent for the Synthesis and Enrichment of Gold Nanoclusters. Nanomaterials, 11 (9): (2258). [PMID:34578574] [10.3390/nano11092258] |
| 16. Yufen Lai, Mengyan Li, Xiaofei Liao, Li Zou. (2021) Smartphone-Assisted Colorimetric Detection of Glutathione and Glutathione Reductase Activity in Human Serum and Mouse Liver Using Hemin/G-Quadruplex DNAzyme. MOLECULES, 26 (16): (5016). [PMID:34443603] [10.3390/molecules26165016] |
| 17. Songlin Liu, Hao Ma, Jinyu Zhu, Xiao Xia Han, Bing Zhao. (2020) Ferrous cytochrome c-nitric oxide oxidation for quantification of protein S-nitrosylation probed by resonance Raman spectroscopy. SENSORS AND ACTUATORS B-CHEMICAL, [PMID:] [10.1016/j.snb.2020.127706] |
| 18. Fengjiao Mao, Kai Yu, Jing He, Qi Zhou, Guangming Zhang, Wenxin Wang, Na Li, Hong Zhang, Jie Jiang. (2019) Real-time monitoring of electroreduction and labelling of disulfide-bonded peptides and proteins by mass spectrometry. ANALYST, 144 (23): (6898-6904). [PMID:31638109] [10.1039/C9AN01420A] |
| 19. Wang Xiaoqing, Sun Qian, Zhao Liming, Gong Shuwen, Xu Li. (2019) Visualization of hydrogen polysulfides in living cells and in vivo via a near-infrared fluorescent probe. JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY, 24 (7): (1077-1085). [PMID:31515622] [10.1007/s00775-019-01718-6] |
| 20. Jian-Yu Yang, Ting Yang, Xiao-Yan Wang, Yi-Ting Wang, Meng-Xian Liu, Ming-Li Chen, Yong-Liang Yu, Jian-Hua Wang. (2019) A Novel Three-Dimensional Nanosensing Array for the Discrimination of Sulfur-Containing Species and Sulfur Bacteria. ANALYTICAL CHEMISTRY, [PMID:30964645] [10.1021/acs.analchem.9b00476] |
| 21. Chengfei Zhao, Xuewen Wang, Lina Wu, Wen Wu, Yanjie Zheng, Liqing Lin, Shaohuang Weng, Xinhua Lin. (2019) Nitrogen-doped carbon quantum dots as an antimicrobial agent against Staphylococcus for the treatment of infected wounds. COLLOIDS AND SURFACES B-BIOINTERFACES, [PMID:30928801] [10.1016/j.colsurfb.2019.03.042] |
| 22. Xingqi Wang, Yong Zhang, Jie Huang, Mengqiu Xia, Liu Liu, Chunling Tian, Rongfeng Hu, Shuangying Gui, Xiaoqin Chu. (2019) Self-assembled hexagonal liquid crystalline gels as novel ocular formulation with enhanced topical delivery of pilocarpine nitrate. INTERNATIONAL JOURNAL OF PHARMACEUTICS, [PMID:30878587] [10.1016/j.ijpharm.2019.02.033] |
| 23. Wang Xingqi, Zhang Yong, Huang Jie, Tian Chunling, Xia Mengqiu, Liu Liu, Li Zhengguang, Cao Jiaojiao, Gui Shuangying, Chu Xiaoqin. (2019) A Novel Phytantriol-Based Lyotropic Liquid Crystalline Gel for Efficient Ophthalmic Delivery of Pilocarpine Nitrate. AAPS PHARMSCITECH, 20 (1): (1-14). [PMID:30603986] [10.1208/s12249-018-1248-0] |
| 24. Shanshan Wang, Xu Hun, Xiliang Luo. (2018) Photoelectrochemical endocrine-disrupting chemicals aptasenor based on resonance energy transfer between SnSe/GR and AuNPs along with GSSG for signal amplification. SENSORS AND ACTUATORS B-CHEMICAL, [PMID:] [10.1016/j.snb.2018.01.074] |
| 25. Huili Ye, Hao Wang, Faqiong Zhao, Baizhao Zeng. (2017) A one-pot hydrothermal synthesis of graphene/CdS:Mn photocatalyst for photoelectrochemical sensing of glutathione. RSC Advances, 7 (72): (45792-45798). [PMID:] [10.1039/C7RA09075G] |
| 26. Zihao Zhang, Yongjing Li, Jiaxun Wan, Peihua Long, Jia Guo, Guosong Chen, Changchun Wang. (2017) Preparation of Pt(IV)-crosslinked polymer nanoparticles with an anti-detoxifying effect for enhanced anticancer therapy. Polymer Chemistry, 8 (15): (2410-2422). [PMID:] [10.1039/C6PY02148D] |
| 27. Lingzhi Zhao, Zhao Li, Liu Zhao, Chenxiao Zhang. (2017) In Vivo Determination of Reduced Thiols in Rat Cerebellum Paraflocculus Following Salicylate-Induced Tinnitus by Fluorescence. ANALYTICAL LETTERS, [PMID:] [10.1080/00032719.2016.1186170] |
| 28. Yinghan Yan, Cuiling Zhang, Wei Gu, Caiping Ding, Xinchang Li, Yuezhong Xian. (2016) Facile Synthesis of Water-Soluble WS2 Quantum Dots for Turn-On Fluorescent Measurement of Lipoic Acid. Journal of Physical Chemistry C, [PMID:] [10.1021/acs.jpcc.6b01868] |
| 29. Shaohua Guo, Grzegorz Maria Popowicz, Daoming Li, Dongjuan Yuan, Yonghua Wang. (2016) Lid mobility in lipase SMG1 validated using a thiol/disulfide redox potential probe. FEBS Open Bio, 6 (5): (477-483). [PMID:27419053] [10.1002/2211-5463.12059] |
| 30. Jingjing Zhao, Kun Zhang, Ji Ji, Baohong Liu. (2016) Sensitive and label-free quantification of cellular biothiols by competitive surface-enhanced Raman spectroscopy. TALANTA, [PMID:26992511] [10.1016/j.talanta.2016.02.008] |
| 31. Lei Ouyang, Lihua Zhu, Jizhou Jiang, Heqing Tang. (2014) A surface-enhanced Raman scattering method for detection of trace glutathione on the basis of immobilized silver nanoparticles and crystal violet probe. ANALYTICA CHIMICA ACTA, [PMID:24580853] [10.1016/j.aca.2014.01.046] |
| 32. Hua-Ying Chen, Yue He, Chao Chen, Jing Wang, Kai Ge, Bin-Bin Chen, Da-Wei Li. (2025) A dual-reactivity-based surface-enhanced Raman spectroscopy nanosensor for the simultaneous imaging of hypochlorite and nitric oxide in living cells. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, [PMID:39983277] [10.1016/j.saa.2025.125899] |
| 33. Jun-Ru Tian, Jie-Yao Song, Zhongchang Wang. (2025) Covalently Coupling Carbon Quantum Dots for Photoluminescence Red Shift Response to pH. INORGANIC CHEMISTRY, [PMID:39920098] [10.1021/acs.inorgchem.4c05129] |
| 34. Mintong Tian, Zehua Li, Purui Yu, Meng Zhou, Mingming Li, Guanghao Li, Qipeng Yuan. (2025) Insights on enhancing the application of glucoraphenin in radish based on the decomposition mechanism. Food Bioscience, [PMID:] [10.1016/j.fbio.2025.106437] |
| 35. Xiuzhen Li, Yuanting Ni, Chenxi Liu, Shaohua Xu, Wei Shu, Hong Liang, Ming Chen. (2025) An electrochemical sensor based on immobilized cystathionine β-synthase (CBS) enzymes and Pd@CuO modified covalent organic framework for specific detection of homocysteine. MICROCHEMICAL JOURNAL, [PMID:] [10.1016/j.microc.2025.113950] |
| 36. Qingfei He, Lingjun Cheng, Yuanyuan Yang, Zhiyan Zou, Canping Su, Xuan Shi, Jiaming Chen, Weirong Huang, Zhenyu Lin, Guolin Hong. (2026) Electrochemiluminescence Biosensor Based on Dual-Signal Regulation of Gold Nanoclusters for Amyloid-β Protein Detection. ANALYTICAL CHEMISTRY, [PMID:41747767] [10.1021/acs.analchem.5c07069] |
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