N-(D,L-erythro,threo-4-fluoroglutamyl)-γ-glutamic acid tri-tert-butyl ester | 124688-51-3

• 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: N-(D,L-erythro,threo-4-fluoroglutamyl)-γ-glutamic acid tri-tert-butyl ester
• CAS: 124688-51-3；124688-52-4；124688-53-5；124688-54-6
• 化学式: C₂₂H₃₉FN₂O₇
• 分子量: 462.559
• InChiKey: JHWKJNVNKJIDQF-NRXISQOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  134.02
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-(D,L-erythro,threo-4-fluoroglutamyl)-γ-glutamic acid tri-tert-butyl ester 在 氰基磷酸二乙酯 、 三乙胺 、 三氟乙酸 作用下， 反应 101.0h， 生成 N--γ-glutamic acid
  参考文献：
  名称：

  Synthesis of N-[N-(4-deoxy-4-amino-10-methylpteroyl)-4-fluoroglutamyl]-.gamma.-glutamate, an unusual substrate for folylpoly-.gamma.-glutamate synthetase and .gamma.-glutamyl hydrolase

  摘要：

  N-[N-(4-Deoxy-4-amino-10-methylpteroyl)-4-fluoroglutamyl]-ga mma-glutamate has been synthesized and its ability to serve as a substrate for folylpolyglutamate synthetase and gamma-glutamyl hydrolase has been investigated. It was anticipated that this compound would be a substrate for both of these enzymes. Although the title compound proved to be a good substrate for folylpolyglutamate synthetase, hydrolysis catalyzed by gamma-glutamyl hydrolase was unexpectedly slow. These results suggest the use of fluoroglutamate-containing peptides as hydrolase-resistant folates or antifols in a variety of chemotherapeutic regimens.

  DOI：

  10.1021/jm00165a021
• 作为产物：
  描述：

  在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 甲醇 、 乙醇 、 氯仿 为溶剂， 25.0 ℃ 、289.58 kPa 条件下， 反应 57.0h， 生成 N-(D,L-erythro,threo-4-fluoroglutamyl)-γ-glutamic acid tri-tert-butyl ester
  参考文献：
  名称：

  Synthesis of N-[N-(4-deoxy-4-amino-10-methylpteroyl)-4-fluoroglutamyl]-.gamma.-glutamate, an unusual substrate for folylpoly-.gamma.-glutamate synthetase and .gamma.-glutamyl hydrolase

  摘要：

  N-[N-(4-Deoxy-4-amino-10-methylpteroyl)-4-fluoroglutamyl]-ga mma-glutamate has been synthesized and its ability to serve as a substrate for folylpolyglutamate synthetase and gamma-glutamyl hydrolase has been investigated. It was anticipated that this compound would be a substrate for both of these enzymes. Although the title compound proved to be a good substrate for folylpolyglutamate synthetase, hydrolysis catalyzed by gamma-glutamyl hydrolase was unexpectedly slow. These results suggest the use of fluoroglutamate-containing peptides as hydrolase-resistant folates or antifols in a variety of chemotherapeutic regimens.

  DOI：

  10.1021/jm00165a021