Girard's P reagent | 13087-67-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Girard's P reagent
• 英文别名: Girard-Reagenz；N--pyridinium；Hydrazidoacetyl-pyridinium；1-hydrazinocarbonylmethyl-pyridinium；2-Pyridin-1-ium-1-ylacetohydrazide
• CAS: 13087-67-7
• 化学式: C₇H₁₀N₃O
• 分子量: 152.176
• InChiKey: HMHYMVIXYCISRO-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  59
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Girard's P reagent 在 sodium cyanoborohydride 作用下， 以 phosphate buffer 为溶剂， 反应 8.67h， 生成
  参考文献：
  名称：

  使用Girard P试剂和强阳离子交换色谱法富集羰基化肽。

  摘要：

  已经显示出蛋白质的氧化修饰形式在氧化应激，衰老以及一些与年龄有关的疾病中积累。通过多种途径进行蛋白质氧化的独特特征之一是羰基的生成。在氧化应激疾病研究中，主要关注的是蛋白质组中的哪些蛋白质被氧化以及氧化位点。基于蛋白质通常通过胰蛋白酶解肽片段表征的事实，本文报道了一种分离氧化肽的方法，该方法包括（1）用吉拉德P试剂（GRP; 1-（2-hydrazino-2 （2-氧代乙基）吡啶鎓氯化物），（2）使用强阳离子交换（SCX）色谱法对衍生肽进行蛋白水解富集后，（3）使用串联质谱法鉴定氧化位。通过使蛋白质羰基与GRP酰肼反应，可以实现氧化蛋白质中醛和酮的衍生化。所得的bond键被氰基硼氢化钠还原，以进一步稳定标记。用模型肽优化了衍生时间和衍生剂的浓度。氧化转铁蛋白被用作模型蛋白质，以研究蛋白质水平上的衍生化效率。在金属催化的转铁蛋白氧化后，该蛋白用GRP衍生化并消化胰蛋白酶。然后用pH 6.0的

  DOI：

  10.1021/ac0514220

文献信息

• Preparation and uses of locked-ring sugar C-glycoside derivatives
  申请人：Price Neil P.

  公开号：US20080081905A1

  公开（公告）日：2008-04-03

  “Locked-ring” C-glycoside derivatives may be prepared wherein the ring of the sugar molecule remains intact without the need for any protecting groups. These C-glycoside derivatives may be produced by first reacting an aldose reducing sugar, which may be a hexose or a pentose, with a β-diketone to form a C-glycoside ketone. The C-glycoside ketone is then reacted with a ketone reactive compound, such as a hydrazine or hydroxylamine, optionally linked to a detectable label, to form a C-glycoside derivative wherein the ketone reactive compound is conjugated to the C-glycoside at the site of the ketone. The aldose reducing sugar used in the first reaction may a simple pentose or hexose monosaccharide, or it may be optionally substituted.

  可以制备“锁定环”C-糖苷衍生物，其中糖分子的环保持完整，无需任何保护基团。这些C-糖苷衍生物可以通过首先将醛糖还原糖（可以是己糖或戊糖）与β-二酮反应以形成C-糖苷酮。然后，将C-糖苷酮与酮反应性化合物（如肼或羟胺，可选地连接到可检测的标记）反应，形成一个C-糖苷衍生物，其中酮反应性化合物与C-糖苷在酮的位置结合。在第一反应中使用的醛糖还原糖可以是简单的戊糖或己糖单糖，也可以是可选择地取代的。
• Process for the preparation of oxidized phospholipids
  申请人：Halperin Gideon

  公开号：US20070112211A1

  公开（公告）日：2007-05-17

  Novel synthetic routes, which are highly applicable for industrial preparation of therapeutically beneficial oxidized phospholipids are disclosed. Particularly, novel methods for efficiently preparing compounds having a glycerolic backbone and one or more oxidized moieties attached to the glycerolic backbone, which are devoid of column chromatography are disclosed. Further disclosed are novel methods of introducing phosphorous-containing moieties such as phosphate moieties to compounds having glycerolic backbone and intermediates formed thereby.

  本发明揭示了一种新的合成路线，非常适用于工业制备具有治疗益处的氧化磷脂类化合物。特别是，本发明揭示了一种高效制备具有甘油骨架和一个或多个氧化基团连接到甘油骨架上的化合物的新方法，该方法不需要使用柱层析。此外，本发明还揭示了将含磷基团（如磷酸盐基团）引入具有甘油骨架和由此形成的中间体的化合物的新方法。
• PROCESS FOR THE PREPARATION OF OXIDIZED PHOSPHOLIPIDS
  申请人：Halperin Gideon

  公开号：US20120130108A1

  公开（公告）日：2012-05-24

  Novel synthetic routes, which are highly applicable for industrial preparation of therapeutically beneficial oxidized phospholipids are disclosed. Particularly, novel methods for efficiently preparing compounds having a glycerolic backbone and one or more oxidized moieties attached to the glycerolic backbone, which are devoid of column chromatography are disclosed. Further disclosed are novel methods of introducing phosphorous-containing moieties such as phosphate moieties to compounds having glycerolic backbone and intermediates formed thereby.

  本发明揭示了一种新型合成路线，适用于工业制备治疗有益的氧化磷脂。特别是，揭示了一种高效制备具有甘油骨架和一个或多个氧化物附着在甘油骨架上的化合物的新方法，这些方法不需要柱层析。此外，还揭示了一种引入含磷基团（如磷酸盐基团）到具有甘油骨架的化合物和由此形成的中间体的新方法。
• Process for the Preparation of Oxidized Phospholipids
  申请人：Vascular Biogenics Ltd.

  公开号：US20130158283A1

  公开（公告）日：2013-06-20

  Novel synthetic routes, which are highly applicable for industrial preparation of therapeutically beneficial oxidized phospholipids are disclosed. Particularly, novel methods for efficiently preparing compounds having a glycerolic backbone and one or more oxidized moieties attached to the glycerolic backbone, which are devoid of column chromatography are disclosed. Further disclosed are novel methods of introducing phosphorous-containing moieties such as phosphate moieties to compounds having glycerolic backbone and intermediates formed thereby.

  揭示了一种新的合成路线，适用于工业制备具有治疗效果的氧化磷脂类化合物。特别是，揭示了一种高效制备具有甘油骨架和一个或多个氧化基团附着在甘油骨架上的化合物的新方法，这些方法不需要使用柱层析法。此外，还揭示了一种引入含磷基团（如磷酸盐基团）到具有甘油骨架的化合物和由此形成的中间体的新方法。
• High-Purity Phospholipids
  申请人：HALPERIN Gideon

  公开号：US20130079540A1

  公开（公告）日：2013-03-28

  Novel synthetic routes, which are highly applicable for industrial preparation of therapeutically beneficial oxidized phospholipids are disclosed. Particularly, novel methods for efficiently preparing compounds having a glycerolic backbone and one or more oxidized moieties attached to the glycerolic backbone, which are devoid of column chromatography are disclosed. Further disclosed are novel methods of introducing phosphorus-containing moieties such as phosphate moieties to compounds having glycerolic backbone and intermediates formed thereby. Further disclosed is substantially pure 1-hexadecyl-2-(4′-carboxy)butyl-sn-glycero-3-phosphocholine (CI-201).

  本发明揭示了一种新的合成路线，非常适用于工业制备治疗上有益的氧化磷脂。特别地，本发明揭示了一种高效制备具有甘油骨架和一个或多个氧化基团附着在甘油骨架上的化合物的新方法，这些方法不需要柱层析。进一步揭示了一种引入含磷基团（如磷酸盐基团）到具有甘油骨架和由此形成的中间体的新方法。进一步揭示了几乎纯的1-十六烷基-2-(4'-羧基)丁基-sn-甘油-3-磷酸胆碱（CI-201）。