五糖醇,3,4-脱水-1,2,5-三脱氧-3-C-甲基-2-硝基-(9CI) | 75007-24-8

• 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: 五糖醇,3,4-脱水-1,2,5-三脱氧-3-C-甲基-2-硝基-(9CI)
• 英文名称: H-Glu-Asp-Gly-OH
• 英文别名: Glutamyl-aspartyl-glycine；(4S)-4-amino-5-[[(2S)-3-carboxy-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 75007-24-8
• 化学式: C₁₁H₁₇N₃O₈
• 分子量: 319.271
• InChiKey: DSPQRJXOIXHOHK-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  196
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  五糖醇,3,4-脱水-1,2,5-三脱氧-3-C-甲基-2-硝基-(9CI) 、 hydrocortisone-21-O-β-carbonylpropionic acid p-nitrophenolic ester 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 以79%的产率得到hydrocortisone-21-O-β-carbonylpropionyl-Glu-Asp-Gly-OH
  参考文献：
  名称：

  The synthesis and immunosuppressive activities of steroid–urotoxin linkers

  摘要：

  The urotoxins (Glu-Asp-Gly-OH, His-Gly-Glu-OH, His-Gly-Lys-OH, and His-Gly-Lys-NHNH2) were introduced into the convenient sites of hydrocortisone and prednisolone via the amidation or condensation reactions to form the corresponding linkers 7a-d, 8a-d, 9a,b, and 10a,b in acceptable yields. The bioassays such as prolongation of heterotopic transplanted cardiac tissue survival in vivo, inhibitory effects on phagocytosis of mouse peritoneal macrophages and concanavalin (ConA) or lipopolysaccharide (LPS) induced proliferation of mouse spleen lymphocytes in vitro show that at the comparable concentrations the immuno suppressive activities of the steroid-urotoxin linkers 7a-d, 8a-d, 9a,b, and 10a,b were higher than that of hydrocortisone, prednisolone, and the urotoxins alone, as well as significantly higher than that of the mixture of hydrocortisone and urotoxins or prednisolone and urotoxins. The so-called 'permissive action' may be responsible for the enhancement of the mentioned bioactivities of the steroid-urotoxin linkers 7a-d, 8a-d, 9a,b, and 10a,b. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.012
• 作为产物：
  描述：

  (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 5-benzyl ester 1-(2,5-dioxo-pyrrolidin-1-yl) ester 在 5%-palladium/activated carbon 、 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 82.17h， 生成 五糖醇,3,4-脱水-1,2,5-三脱氧-3-C-甲基-2-硝基-(9CI)
  参考文献：
  名称：

  PHARMACEUTICAL COMPOSITION COMPRISING THE PEPTIDE GLU-ASP-GLY AND USE FOR TREATING HELICOBACTER PYLORI INDUCED GASTRODUODENAL DISEASES

  摘要：

  公开号：

  EP2667887B1

文献信息

• Characterization of an acidic tripeptide in neurotoxic dialysate.
  作者：TAKASHI ABIKO、IKUKO ONODERA、HIROSHI SEKINO

  DOI：10.1248/cpb.28.1629

  日期：——

  An acidic tripeptide was isolated from neurotoxic dialysate by ultrafiltration with an Amicon Centriflo DM-5 membrane, followed by gel filtration on Sephadex G-15 and Sephadex G-10, and ion-exchange chromatography on DEAE-Sephadex A-25. The tripeptide thus obtained was identified as H-Glu-Asp-Gly-OH by amino acid analysis, Edman degradation, and measurement of physical constants and analytical data in comparison with those of the authentic tripeptide. This tripeptide inhibited LDH activity.

  通过Amicon Centriflo DM-5膜超滤，从神经毒性透析液中分离出一种酸性三肽，随后在Sephadex G-15和Sephadex G-10上进行凝胶过滤，并在DEAE-Sephadex A-25上进行离子交换色谱。通过氨基酸分析、EDMan降解以及物理常数和与真三肽的分析数据比较，确定所获得的三肽为H-Glu-Asp-Gly-OH。该三肽可抑制LDH活性。
• PEPTIDE SUBSTANCE REVEALING A STRESS PROTECTIVE EFFECT, PHARMACEUTICAL COMPOSITION ON ITS BASE, AND THE METHOD OF ITS APPLICATION
  申请人：Khavinson Vladimir Khatskelevich

  公开号：US20090105158A1

  公开（公告）日：2009-04-23

  The invention is related to the medicinal means of prevention and treatment for functional or stress induced disorders, which occur as a result of extreme impacts, and may be used as a medication revealing a stress protective effect. There is proposed a peptide glutamyl-aspartyl-glycine with general formula H-Glu-Asp-Gly-OH sequence 1 [SEQ ID NO:1], revealing a stress protective effect. There is proposed a pharmaceutical composition revealing a stress protective effect, characterized in that such composition contains an effective amount of peptide glutamyl-aspartyl-glycine with general formula H-Glu-Asp-Gly-OH sequence 1 [SEQ ID NO:1] as its active base, as well as a pharmaceutically acceptable carrier. In this case such pharmaceutical composition exists in the form suitable for parenteral or intranasal administration. There is proposed a method of prevention and/or treatment for functional or stress induced disorders, which occur as a result of extreme impacts, such method consisting in the administration to a patient of a pharmaceutical composition containing an effective amount of peptide glutamyl-aspartyl-glycine with general formula H-Glu-Asp-Gly-OH sequence 1 [SEQ ID NO:1] as its active base in the dose of 0.01-100 μg/kg of body weight, at least once a day during a period necessary for attaining a therapeutic effect. In this case such administration is performed parenterally or intranasally.

  本发明涉及预防和治疗由极端影响引起的功能或压力诱发的疾病的药物手段，并可用作具有应激保护作用的药物。提出了一种具有一般式H-Glu-Asp-Gly-OH序列1 [SEQ ID NO：1]的肽谷氨酰天冬氨酸甘氨酸，具有应激保护作用。提出了一种具有应激保护作用的制药组合物，其特征在于该组合物含有有效量的一般式为H-Glu-Asp-Gly-OH序列1 [SEQ ID NO：1]的肽谷氨酰天冬氨酸甘氨酸作为其活性基，并含有一种药学上可接受的载体。在这种情况下，这种制药组合物以适合于肌肉注射或鼻腔给药的形式存在。提出了一种预防和/或治疗由极端影响引起的功能或压力诱发的疾病的方法，该方法包括向患者注射含有效量的一般式为H-Glu-Asp-Gly-OH序列1 [SEQ ID NO：1]的肽谷氨酰天冬氨酸甘氨酸作为其活性基的制药组合物，剂量为0.01-100μg / kg体重，每天至少一次，直到达到治疗效果所需的时间为止。在这种情况下，此类给药是通过肌肉注射或鼻腔给药进行的。
• Chemical isotope labeling-assisted liquid chromatography-mass spectrometry enables sensitive and accurate determination of dipeptides and tripeptides in complex biological samples
  作者：Feng-Qing Huang、Yu Wang、Ji-Wen Wang、Dai Yang、Shi-Lei Wang、Yuan-Ming Fan、Raphael N. Alolga、Lian-Wen Qi

  DOI：10.1016/j.cclet.2024.109670

  日期：2024.11

  their unique features and diverse biological functions. Achieving rapid separation and accurate quantification, however, remains a challenge because of their low abundance and the co-existence of numerous structural isomers. In this study, we developed a novel approach using isotope chemical labeling for ultrasensitive determination of di/tripeptides in biological samples. We successfully synthesized a

  小肽因其独特的特性和多样化的生物学功能而受到越来越多的关注。然而，由于其丰度低且存在多种结构异构体，实现快速分离和准确定量仍然是一个挑战。在这项研究中，我们开发了一种使用同位素化学标记超灵敏测定生物样品中二肽/三肽的新方法。我们成功合成了一种新型衍生化试剂4-(2-(乙氧基亚甲基)-3-氧代丁酰胺基)-三甲基苯胺碘化物(EOTMBA)及其氘标记同位素试剂(-EOTMBA)。总共97个小肽，包括89个二肽和8个三肽，在60℃下1.5小时内可以在​​甲醇中完全衍生化。 EOTMBA 标记后，通过 LC-MS/MS 分析在 22 分钟内完成对这些二肽/三肽的分析。该方法的准确度为 86.3%–113%，定量限范围为 0.25 fmol/L 至 5 nmol/L。利用该方法，我们对取自健康个体和胆道疾病患者的 147 份血浆、49 份尿液和 46 份胆汁样本中的二肽/三肽进行了超灵敏和准确的定量。
• PEPTIDE SUBSTANCE REVEALING A STRESS PROTECTIVE EFFECT, PHARMACEUTICAL COMPOSITION ON ITS BASE AND THE METHOD OF ITS APPLICATION
  申请人：Obschestvo S Ogranichennoi Otvetstvennostyu "sia Peptides"

  公开号：EP2021353A2

  公开（公告）日：2009-02-11
• US8071556B2
  申请人：——

  公开号：US8071556B2

  公开（公告）日：2011-12-06