dibenzyl tosylate of L-glutamic acid | 130289-55-3

• 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: dibenzyl tosylate of L-glutamic acid
• 英文别名: dibenzyl ester of L-glutamic acid p-toluenesulfonate；Tosyl-Glu(OBn)-OBn；α,γ-Dibenzyl-L-glutamat-tosylat；N-p-Toluolsulfonyl-L-glutaminsaeure-dibenzylester；dibenzyl (2S)-2-[(4-methylphenyl)sulfonylamino]pentanedioate
• CAS: 130289-55-3
• 化学式: C₂₆H₂₇NO₆S
• 分子量: 481.569
• InChiKey: KPPFTSJRZQQQBX-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dibenzyl tosylate of L-glutamic acid 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 N-(2-naphthyl)acetylglutamic acid
  参考文献：
  名称：

  CNS stimulant effect of N-acylderivatives of glutamic and aspartic acids

  摘要：

  DOI：

  10.1007/bf00766247

文献信息

• A class of novel conjugates of substituted purine and Gly-AA-OBzl: Synthesis and evaluation of orally analgesic activity
  作者：Guifeng Kang、Ming Zhao、Xiaoyi Zhang、Li Peng、Chunbo Li、Wei Mao、Weidong Ye、Shiqi Peng

  DOI：10.1016/j.bmcl.2009.05.077

  日期：2010.10

  five-step-reaction procedure and 19 novel conjugates N-[2-chloro-9-(tetrahydropyran-2-yl)-9H-purin-6-yl]-N-cyclopropylglycylamino acid benzylesters were provided. On mouse-tail flick model their in vivo analgesic activities were assayed. The results indicate that introducing Gly-OC2H5 into the 6-position of the substituted purine leads to ambiguous increase of the analgesic activity, while introducing Gly-AA-OBzl

  针对慢性疼痛的化学疗法，通过五步反应方法和19种新型缀合物N- [2-氯-9-（四氢吡喃-2-）偶联了两种止痛药，取代的嘌呤和Gly-AA-OBzl。提供了（yl）-9 H-嘌呤-6-yl] -N-环丙基糖基氨基酸苄酯。在鼠尾轻弹模型上，测定了它们的体内止痛活性。结果表明，将Gly-OC 2 H 5引入取代的嘌呤的6-位导致镇痛活性的模棱两可的增加，而将Gly-AA-OBzl引入该位置导致镇痛活性的显着增加。
• Hydrogen fluoride-anisole catalyzed reaction with glutamic acid containing peptides
  作者：Seiyo Sano、Shosuke Kawanishi

  DOI：10.1021/ja00845a033

  日期：1975.6
• Toltsikov, V. V.; Kwi, Hwang Heng; Zvonkova, E. N., Journal of general chemistry of the USSR, 1986, vol. 56, p. 1460 - 1463
  作者：Toltsikov, V. V.、Kwi, Hwang Heng、Zvonkova, E. N.、Evstigneeva, R. P.

  DOI：——

  日期：——
• Rationally Designed Sulfamides as Glutamate Carboxypeptidase II Inhibitors
  作者：Cindy J. Choy、Melody D. Fulton、Austen L. Davis、Mark Hopkins、Joseph K. Choi、Marc O. Anderson、Clifford E. Berkman

  DOI：10.1111/cbdd.12174

  日期：2013.11

  Glutamate carboxypeptidase II (GCPII) is a membrane‐bound cell surface peptidase. There is significant interest in the inhibition of GCPII as a means of neuroprotection, while GCPII inhibition as a method to treat prostate cancer remains a topic of further investigation. The key zinc‐binding functional group of the well‐characterized classes of GCPII inhibitors (phosphonates and phosphoramidates) is tetrahedral and negatively charged at neutral pH, while glutamyl urea class of inhibitors possesses a planar and neutral zinc‐binding group. This study explores a new class of GCPII inhibitors, glutamyl sulfamides, which possess a putative net neutral tetrahedral zinc‐binding motif. A small library containing six sulfamides was prepared and evaluated for inhibitory potency against purified GCPII in an enzymatic assay. While most inhibitors have potencies in the micromolar range, one showed promising sub‐micromolar potency, with the optimal inhibitor in this series being aspartyl–glutamyl sulfamide (2d). Lastly, computational docking was used to develop a tentative binding model on how the most potent inhibitors interact with the ligand‐binding site of GCPII.
• WANG, Y. H.;XU, J. C., SYNTHESIS,(1990) N, C. 845-846
  作者：WANG, Y. H.、XU, J. C.

  DOI：——

  日期：——