glutathione | 35436-84-1

• 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
• 英文名称: glutathione
• 英文别名: Glutathion；Glu-Cys-Gly；γ-L-glutamyl-L-cysteinylglycine；HGluCysGlyOH；ECG；GSH；Glutamyl-cysteinyl-glycine；(4S)-4-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 35436-84-1
• 化学式: C₁₀H₁₇N₃O₆S
• 分子量: 307.327
• InChiKey: ZZIFPJZQHRJERU-WDSKDSINSA-N

物化性质

• 沸点：
  756.4±60.0 °C(Predicted)
• 密度：
  1.441±0.06 g/cm3(Predicted)
• 熔点：
  152-153 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 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：
  160
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  glutathione 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 7Z,9E,11E,14Z-LTC₄
  参考文献：
  名称：

  7Z，9E，11E，14Z-白三烯的合成。

  摘要：

  DOI：

  10.1002/ardp.19843170716
• 作为产物：
  描述：

  S-benzyl-L-cysteinylglycine 在 吡啶 、 氨 、 sodium 作用下， 生成 glutathione
  参考文献：
  名称：

  du Vigneaud; Loring; Miller, Journal of Biological Chemistry, 1937, vol. 118, p. 391,393

  摘要：

  DOI：

文献信息

• A General and Chemoselective Synthesis of Phosphoramidates through Reaction of Silylated Nucleoside Di- and Triphosphates with Silylated Amines Containing Multifunctional Groups
  作者：Jigang Zhu、Hua Fu、Yuyang Jiang、Yufen Zhao

  DOI：10.1021/jo0521403

  日期：2006.2.1

  phosphoramidates has been developed through one-pot chemoselective reaction of nucleoside di- and triphosphates with 3‘-amino-3‘-deoxythymidine, d-glucosamine, and peptides mediated by trimethylsilyl chloride, and the corresponding conjugates via the linkage of phosphate were obtained. The method could be generally applied for the synthesis of phosphoramidates without any preprotection of polyphosphates and amines

  通过二磷酸核苷和三磷酸核苷与3'-氨基-3'-脱氧胸苷，d-葡糖胺和由三甲基甲硅烷基氯介导的肽以及相应的缀合物通过一键连接的一锅化学选择反应，已经开发出了多种氨基甲酸酯的方法。获得了磷酸盐。该方法通常可用于合成氨基磷酸酯而无需对含多官能团的多磷酸盐和胺进行任何预保护。
• Fluorescent 1.4-Dihydropyridines: The Malondlaldehyde connection
  作者：Vasu Nalr、Rick J. Offerman、Gregory A. Turner、Alton N. Pryor、Norman C. Baenzlger

  DOI：10.1016/s0040-4020(88)90015-4

  日期：1988.1

  malondlaldehyde Is capable of modifying amino acid residues to novel, highly fluorescent 1,4-dihydropyridines. The structures assigned to these compounds are supported by UV, HRMS, high-field NMR, and X-ray crystallographic data. The mechanism of these transformations, which Is fully discussed, involves the Michael reaction of alkylidene malondialdehydes with enaminals, both of which are produced as detectable

  在合适的条件下，丙二醛能够将氨基酸残基修饰为新型的高荧光1,4-二氢吡啶。分配给这些化合物的结构受到UV，HRMS，高场NMR和X射线晶体学数据的支持。充分讨论了这些转化的机理，涉及亚烷基丙二醛与烯胺的迈克尔反应，二者均以可检测的中间体形式产生。这些发现对于解释丙二醛的某些生物化学可能具有重要意义。该转化也提供了一种新的合成方法，该方法可以合成广泛潜在的作为钙通道拮抗剂的光稳定的4-芳基化的1-芳基-1,4-dlhydropyridines。
• Studies on the formation of reactive intermediates from the antineoplastic agentN,N′Bis(2-chloroethyl)-N-nitrosourea (BCNU)in vitro andin Vivo. Characterization of novel glutathione adducts by ionspray tandem mass spectrometry
  作者：Margaret R. Davis、Thomas A. Baillie

  DOI：10.1002/jms.1190300111

  日期：1995.1

  In a study designed to examine the nature of short-lived, electrophilic intermediates liberated during decomposition of N,N′-bis(2-chloroethyl)-N-nitrosourea (BCNU) in vitro and also on administration of BCNU (140 μmol i.p.) to rats in vivo, both on-line and off-line LC/MS/MS techniques were employed to detect and characterize the corresponding glutathione (GSH) adducts present in incubation media and excreted into bile, respectively. In vitro, four GSH conjugates were formed and these were identified, on the basis of their product ion spectra, as products of S-and N-carbamoylation and alkylation reactions. Although the relative proportions of these in vitro adducts were found to depend on the molar ratios of GSH and BCNU, the major adduct under all conditions studied proved to be S-(2-chloroethylcarbamoyl)glutathione (SCG). Analysis of untreated bile samples by means of on-line LC/MS/MS with constant neutral loss (129 u) and precursor ion (m/z 179) scanning techniques again led to the detection of four GSH conjugates, although only one of these (SCG) was common to the group of adducts identified in vitro. All of the GSH conjugates detected in bile represented products of S-carbamoylation, indicating that the alkylating moiety released from BCNU undergoes reactions in vivo with nucleophiles other than GSH.

  在一项旨在研究N,N'-双(2-氯乙基)-N-亚硝基脲(BCNU)在体外分解过程中释放的短寿命、亲电性中间体的性质以及BCNU(140μmol，腹腔注射)在体内对大鼠的影响的研究中，采用了在线和离线的液相色谱-质谱-质谱(LC/MS/MS)技术，分别检测和表征了存在于培养介质中和排入胆汁中的相应谷胱甘肽(GSH)加合物。在体外，形成了四种GSH结合物，根据其产物离子谱，这些结合物被鉴定为S-和N-氨甲酰化和烷基化反应的产物。尽管这些体外加合物的相对比例取决于GSH和BCNU的摩尔比，但在所有研究条件下，主要的加合物均为S-(2-氯乙基氨甲酰)谷胱甘肽(SCG)。通过使用具有恒定中性损失(129u)和母体离子(m/z 179)扫描技术的在线LC/MS/MS分析未经处理的胆汁样本，再次检测到了四种GSH加合物，尽管其中只有一种(SCG)与体外鉴定出的加合物组相同。所有在胆汁中检测到的GSH加合物均代表S-氨甲酰化的产物，这表明从BCNU释放出的烷基化部分在体内与除GSH以外的亲核试剂发生了反应。
• Reaction of [18F]4-fluorobenzenediazonium cations with cysteine or the cysteinyl group: preparation of18F-labeled S-aryl-cysteine and a radiolabeled peptide
  作者：J. T. Patt、M. Patt

  DOI：10.1002/jlcr.635

  日期：2002.12

  A reaction route for the preparation of no-carrier-added (n.c.a.) [18F]S-4-fluorophenylcysteine 7 via the [18F]-4-fluorobenzenediazonium ion 4 is described. The key step in this radiosynthesis is the reaction of 4 with cysteine forming [18F]4-fluorophenyldiazocysteine 6, which is subsequently converted into 7 by irradiation with 366 nm light. 4 was synthesized by reacting 1,4-dinitrobenzene 1 with [18F]-fluoride in acetonitrile in a PEEK-capillary in a microwave oven. After dilution of the reaction mixture with methanol, the resulting [18F]4-fluoro-1-nitrobenzene 2 was submitted to reduction by means of H2 with Pd on C catalyst. The resulting [18F]4-fluoroaniline 3 was purified by HPLC and diazotized to 4. The preparation of 4 was optimized with regard to yield and purity. The radiochemical yield of 6 was >90% (based on 3) while after UV irradiation and HPLC purification 45% of 7 (based on 3) was obtained (yields corrected for decay). The suitability of this method for labeling peptides with fluorine-18 was demonstrated by application to the tripeptide, glutathione (GSH; γ-L-glutamyl-L-cysteinyglycine) 8. Copyright © 2002 John Wiley & Sons, Ltd.

  描述了一种通过[18F]-4-氟苯二氮离子4制备无载体添加（n.c.a.）[18F]S-4-氟苯丙氨酸7的反应路线。本放射合成的关键步骤是4与半胱氨酸反应形成[18F]4-氟苯基二氮半胱氨酸6，随后通过366纳米光照射转化为7。4的合成是通过将1,4-二硝基苯1与[18F]-氟化物在微波炉中的PEEK毛细管中于乙腈中反应得到的。在用甲醇稀释反应混合物后，得到的[18F]4-氟-1-硝基苯2通过Pd/C催化剂与氢气还原。得到的[18F]4-氟苯胺3经过HPLC纯化并重氮化为4。4的制备在产率和纯度上得到了优化。6的放射化学产率超过90%（基于3），而在紫外线照射和HPLC纯化后，获得了7的产率为45%（基于3，已校正衰变）。通过应用于三肽谷胱甘肽（GSH；γ-L-谷氨酸-L-半胱氨酸-甘氨酸）8，证明了该方法在用氟-18标记肽类方面的适用性。版权 © 2002 John Wiley & Sons, Ltd.
• Synthesis of Leukotriene Analogs
  作者：Bernd Spur、Attilio Crea、Wilfried Peters、Wolfgang König

  DOI：10.1002/ardp.19843170714

  日期：——

  The synthesis of the C20 and C22 analogs of the leukotrienes from the unsaturated aldehydes 2a, b with undecyl(triphenyl)phosphorane and reactions with thiopeptides providing the conjugates LTC, LTD, and LTE is described. Synthese von Leukotrien-Analogen Die Synthese vn C20 and C22 Analogen der Leukotriene aus den ungesattigten Aldehyden 2a, b mit Undecyltriphenylphosphoran und Reaktionen mit Thiopeptiden

  描述了从不饱和醛 2a、b 与十一烷基（三苯基）正膦合成白三烯的 C20 和 C22 类似物，以及与提供缀合物 LTC、LTD 和 LTE 的硫肽反应。白三烯类似物的合成描述了从不饱和醛 2a、b 与十一烷基三苯基膦合成白三烯的 C20 和 C22 类似物，以及与硫肽反应生成缀合物 LTC、LTD 和 LTE。