谷胱甘肽酰胺 | 82147-51-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 谷胱甘肽酰胺
• 中文别名: 硫黄亚酸酸,盐金钠
• 英文名称: γGlu-Cys-Gly-NH2
• 英文别名: glutathione amide；GASH；γECG-NH2；N-[(4S)-4-azaniumyl-4-carboxylatobutanoyl]-L-cysteinylglycinamide；(2S)-5-[[(2R)-1-[(2-amino-2-oxoethyl)amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-2-azaniumyl-5-oxopentanoate
• CAS: 82147-51-1
• 化学式: C₁₀H₁₈N₄O₅S
• 分子量: 306.343
• InChiKey: FBCIXVYKFFJYFT-WDSKDSINSA-N

物化性质

• 沸点：
  775.0±60.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  谷胱甘肽酰胺 以 水 为溶剂， 生成 (γECG-NH2)2
  参考文献：
  名称：

  谷胱甘肽二硫化物的Zn（II）配合物：稳定性增加的结构基础

  摘要：

  谷胱甘肽二硫化物（GSSG）是谷胱甘肽（GSH）的长期被忽视的氧化还原伙伴，被认为参与细胞内锌稳态。我们对GSSG（（γECG）2）及其9个具有C末端修饰的类似物，三肽二硫化物：（γECS）2，（γECE）的一系列类似物的质子化和Zn（II）结合特性进行了协同的电位计和NMR光谱研究。2，（γECG-NH 2）2，（γECG-OET）2，和（γEcG）2 ; 二肽二硫化物（γEC）2和（γEC-OEt）2; 以及混合的二硫化物γECG-γEC和γECG-γEC-OEt。这组化合物中的酸碱和Zn（II）络合特性与平均C端静电荷严格相关。特别地，已证明GSSG在中性pH下在溶液中呈弯曲（头对尾）构象，这由Glu残基的质子化γ-氨基与去质子化的C端Gly羧酸盐之间的静电吸引控制。这种相互作用通过影响氨基的碱度间接地和直接通过Gly羧酸盐参与Zn（II）离子的外部配位域的参与，间接调节GSSG配位

  DOI：

  10.1021/ic101212y

文献信息

• Evolving new molecular function
  申请人：The President and Fellows of Harvard College

  公开号：US20040180412A1

  公开（公告）日：2004-09-16

  Nature evolves biological molecules such as proteins through iterated rounds of diversification, selection, and amplification. The power of Nature and the flexibility of organic synthesis are combined in nucleic acid-templated synthesis. The present invention provides a variety of template architectures for performing nucleic acid-templated synthesis, methods for increasing the selectivity of nucleic acid-templated reactions, methods for performing stereoselective nucleic acid-templated reactions, methods of selecting for reaction products resulting from nucleic acid-templated synthesis, and methods of identifying new chemical reactions based on nucleic acid-templated synthesis.

  大自然通过反复的多样化、选择和放大，使蛋白质等生物分子不断进化。大自然的力量和有机合成的灵活性在核酸模板合成中得到了结合。本发明提供了进行核酸模板合成的各种模板结构、提高核酸模板反应选择性的方法、进行立体选择性核酸模板反应的方法、选择核酸模板合成产生的反应产物的方法，以及基于核酸模板合成鉴定新化学反应的方法。
• Characterization of Glutathione Amide Reductase from Chromatium gracile
  作者：Bjorn Vergauwen、Frederik Pauwels、Françoise Jacquemotte、Terrance E. Meyer、Michael A. Cusanovich、Robert G. Bartsch、Jozef J. Van Beeumen

  DOI：10.1074/jbc.m102026200

  日期：2001.6

  Among the Chromatiaceae, the glutathione derivative gamma -L-glutamyl-L-cysteinylglycine amide, or glutathione amide, was reported to be present in facultative aerobic as well as in strictly anaerobic species, The gene (garB) encoding the central enzyme in glutathione amide cycling, glutathione amide reductase (GAR), has been isolated from Chromatium gracile, and its genomic organization has been examined. The garB gene is immediately preceded by an open reading frame encoding a novel 27.5-kDa chimeric enzyme composed of one N-terminal peroxiredoxin-like domain followed by a glutaredoxin-like C terminus. The 27.5-kDa enzyme was established in vitro to be a glutathione amide-dependent peroxidase, being the first example of a prokaryotic low molecular mass thiol-dependent peroxidase, Amino acid sequence alignment of GAR with the functionally homologous glutathione and trypanothione reductases emphasizes the conservation of the catalytically important redox-active disulfide and of regions involved in binding the FAD prosthetic group and the substrates glutathione amide disulfide and NADH, By establishing Michaelis constants of 97 and 13.2 muM for glutathione amide disulfide and NADH, respectively (in contrast to K-m values of 6.9 mM for glutathione disulfide and 1.98 mM for NADPH), the exclusive substrate specificities of GAR have been documented. Specificity for the amidated disulfide cofactor partly can be explained by the substitution of Arg-37, shown by x-ray crystallographic data of the human glutathione reductase to hydrogen-bond one of the glutathione glycyl carboxylates, by the negatively charged Glu-21, On the other hand, the preference for the unusual electron donor, to some extent, has to rely on the substitution of the basic residues Arg-218, His-219, and Arg-224, which have been shown to interact in the human enzyme with the NADPH 2'-phosphate group, by Leu-197, Glu-198, and Phe-203, We suggest GAR to be the newest member of the class I flavoprotein disulfide reductase family of oxidoreductases.
• Crystallization and preliminary X-ray crystallographic analysis of glutathione amide reductase from<i>Chromatium gracile</i>
  作者：Bjorn Vergauwen、Filip Van Petegem、Han Remaut、Frederik Pauwels、Jozef J. Van Beeumen

  DOI：10.1107/s0907444901020303

  日期：2002.2.1

  The Chromatiaceae-specific glutathione amide reductase (GAR) belongs to the well known family of the glutathione reductases, even though differences in both substrate (glutathione amide instead of glutathione) and coenzyme (NADH instead of NADPH) specificities are reported. Crystals of the GAR enzyme from Chromatium gracile have been grown at 294 K by the hanging-drop vapour-diffusion method using lithium sulfate as a precipitant in the presence of nickel ions. The crystals belong to space group P4(1), with unit-cell parameters a = b = 71.93, c = 223.85 Angstrom, alpha = beta = gamma = 90degrees and one dimer per asymmetric unit. A full set of X-ray diffraction data was collected to 2.1 degrees resolution with a completeness of 95.2%. Structure determination via the method of molecular replacement is under way.
• EP1540013A4
  申请人：——

  公开号：EP1540013A4

  公开（公告）日：2006-06-28
• EVOLVING NEW MOLECULAR FUNCTION
  申请人：The President and Fellows of Harvard College

  公开号：EP1540013B1

  公开（公告）日：2015-07-08