400-998-5282
专注多肽 服务科研
400-998-5282
专注多肽 服务科研
Cu(II) and Ni(II)-binding tripeptide.The Ni(II) complex of GGH was shown by Brown et al. to mediate protein crosslinking by oxidants. GGH has been used in biosensors for the electrochemical detection of Cu(II) ions.
编号：161519
CAS号：7451-76-5/93404-95-6
单字母：H2N-GGH-OH
| 编号: | 161519 |
| 中文名称: | 三肽Gly-Gly-His |
| 中文同义词: | 甘氨酰甘氨酰-L-组氨酸 |
| 英文名: | Gly-Gly-His |
| 英文同义词: | (S)-2-(2-(2-Aminoacetamido)acetamido)-3-(1H-imidazol-4-yl)propanoicacid、 |
| CAS号: | 7451-76-5/93404-95-6 |
| 单字母: | H2N-GGH-OH |
| 三字母: | H2N N端氨基：N-terminal amino group。在肽或多肽链中含有游离a-氨基的氨基酸一端。在表示氨基酸序列时，通常将N端放在肽链的左边。 -Gly甘氨酸：glycine。系统命名为 2-氨基乙酸。是编码氨基酸中没有旋光性的最简单的氨基酸，因具有甜味而得名。符号：G，Gly。 -Gly甘氨酸：glycine。系统命名为 2-氨基乙酸。是编码氨基酸中没有旋光性的最简单的氨基酸，因具有甜味而得名。符号：G，Gly。 -HisL-组氨酸：histidine。系统命名为(2S)-氨基-3-(4-咪唑基)丙酸。其侧链带有弱碱性的咪唑基，为编码氨基酸。是幼小哺乳动物的必需氨基酸。符号：H，His。 -OHC端羧基：C-terminal carboxyl group。在肽或多肽链中含有游离羧基的氨基酸一端。在表示氨基酸序列时，通常将C端放在肽链的右边。 |
| 氨基酸个数: | 3 |
| 分子式: | C10H15N5O4 |
| 平均分子量: | 269.26 |
| 精确分子量: | 269.11 |
| 等电点(PI): | - |
| pH=7.0时的净电荷数: | 1.21 |
| 平均亲水性: | -0.5 |
| 疏水性值: | -1.33 |
| 外观与性状: | 白色粉末状固体 |
| 沸点: | 813.8±65.0°Cat760mmHg |
| 熔点: | >210°C |
| 消光系数: | - |
| 来源: | 人工化学合成，仅限科学研究使用，不得用于人体。 |
| 纯度: | 95%、98% |
| 盐体系: | 可选TFA、HAc、HCl或其它 |
| 生成周期: | 2-3周 |
| 储存条件: | 负80℃至负20℃ |
| 标签: | 三肽 |
| 参考文献（References）: | <ALLPEPTIDE>Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.<ALLPEPTIDE>Arkadiusz Gruchlik, et al. Effect of Gly-Gly-His, Gly-His-Lys and their copper complexes on TNF-alpha-dependent IL-6 secretion in normal human dermal fibroblasts. Acta Pol Pharm. 2012 Nov-Dec;69(6):1303-6.<ALLPEPTIDE>Brandon J Green, et al. Nickel(III) oxidation of its glycylglycylhistamine complex. Dalton Trans. 2004 Nov 7:(21):3508-14.<ALLPEPTIDE>K C Brown, et al. Determining protein-protein interactions by oxidative cross-linking of a glycine-glycine-histidine fusion protein. Biochemistry. 1998 Mar 31;37(13):4397-406.<ALLPEPTIDE>K C Brown, et al. Highly specific oxidative cross-linking of proteins mediated by a nickel-peptide complex. Biochemistry. 1995 Apr 11;34(14):4733-9. |
| TPSA: | 150.2 |
| LogP : | -2.4035 |
| H_Acceptors: | 5.0 |
| H_Donors: | 5.0 |
| Rotatable_Bonds: | 7.0 |
| 警示词: | Warning |
| 危险申明: | H302-H315-H319-H335 |
| 警告申明: | P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501 |
| GHS编码: | GHS07 |
| SMILES: | O=C(O)[C@@H](NC(CNC(CN)=O)=O)CC1=CNC=N1 |
Cu(II) and Ni(II)-binding tripeptide.The Ni(II) complex of GGH was shown by Brown et al. to mediate protein crosslinking by oxidants. GGH has been used in biosensors for the electrochemical detection of Cu(II) ions.
H‑Gly‑Gly‑His‑OH 的生化应用核心为组氨酸金属结合与质子化性质。甘氨酸残基提供高度构象自由度。结构行为有助于催化与折叠通路分析。应用包括配位化学与酶模拟。
H-Gly-Gly-His-OH centers its biochemical utility on histidine’s metal-binding and protonation properties. Glycine residues allow extensive conformational freedom. Structural behavior aids analysis of catalytic and folding pathways. Applications include coordination chemistry and enzymatic modeling.
Gly-Gly-His(GGH)三肽显示出铜(Cu2+)络合的亲和力。这些复合物表现出良好的皮肤耐受性，可用于伤口愈合。通过对成纤维细胞的体内研究，提出GGH铜复合物可减少基于肿瘤坏死因子α(TNF-α)的白细胞介素6(IL-6)分泌。GGH用于与其他含咪唑肽（如肌肽）的比较研究。一个活跃的应用研究领域涉及铜离子的GGH结合。
| DOI | 名称 | |
|---|---|---|
| 10.1039/b212881k | Exploring the use of the tripeptide Gly-Gly-his as a selective recognition element for the fabrication of electrochemical copper sensors | 下载 |
| 10.1021/es049234z | Detection of heavy metal ions in drinking water using a high-resolution differential surface plasmon resonance sensor | 下载 |
| 10.1039/b511081e | Inactivation of human angiotensin converting enzyme by copper peptide complexes containing ATCUN motifs | 下载 |
| 10.1039/b507216f | Oxidative DNA damage induced by autoxidation of microquantities of S(IV) in the presence of Ni(II)-Gly-Gly-His | 下载 |
| 10.1021/bi060348s | Evidence for rapid inter- and intramolecular chlorine transfer reactions of histamine and carnosine chloramines: implications for the prevention of hypochlorous-acid-mediated damage | 下载 |
| 10.1021/la7016243 | Complexation of copper ions with histidine-containing tripeptides immobilized on solid surfaces | 下载 |
| 10.1016/j.bios.2009.05.035 | Electrochemical analysis of copper ion using a Gly-Gly-His tripeptide modified poly(3-thiopheneacetic acid) biosensor | 下载 |
| 10.1016/j.bios.2010.06.030 | Polypyrrole nanowire modified with Gly-Gly-His tripeptide for electrochemical detection of copper ion | 下载 |
| 10.1021/jm4009345 | N- versus C-domain selectivity of catalytic inactivation of human angiotensin converting enzyme by lisinopril-coupled transition metal chelates | 下载 |
| 10.1007/s00775-014-1190-x | Inactivation of sortase A mediated by metal ATCUN complexes | 下载 |
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