H-Glu(α-OtBu)(γ-OTMSE) | 510713-97-0

• 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: H-Glu(α-OtBu)(γ-OTMSE)
• 英文别名: 1-O-tert-butyl 5-O-(2-trimethylsilylethyl) (2S)-2-aminopentanedioate
• CAS: 510713-97-0
• 化学式: C₁₄H₂₉NO₄Si
• 分子量: 303.474
• InChiKey: ZWOIUXVRDDTITA-NSHDSACASA-N

物化性质

• 沸点：
  345.6±32.0 °C(Predicted)
• 密度：
  0.990±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  H-Glu(α-OtBu)(γ-OTMSE) 在 palladium on activated charcoal 4-二甲氨基吡啶 、 四丁基氟化铵 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-[(S)-1-Carboxy-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-2-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyric acid
  参考文献：
  名称：

  N-Me-pAB-Glu-γ-Glu-γ-Tyr(3-NO2): an internally quenched fluorogenic γ-glutamyl hydrolase substrate

  摘要：

  A gamma -glutamyl tripeptide containing an internally quenched fluorophore has been synthesized and shown to be a substrate for recombinant rat gamma -glutamyl hydrolase. HPLC, LC-MS, and fluorescence spectra support the conclusion that selective hydrolysis occurs at the penultimate peptide bond. Preliminary data indicate that hydrolysis of this substrate can be monitored continuously to yield steady-state kinetic data (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00103-2
• 作为产物：
  描述：

  (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-(2-trimethylsilanyl-ethyl) ester 在 palladium on activated charcoal 氢气 、 氢气 作用下， 生成 H-Glu(α-OtBu)(γ-OTMSE)
  参考文献：
  名称：

  N-Me-pAB-Glu-γ-Glu-γ-Tyr(3-NO2): an internally quenched fluorogenic γ-glutamyl hydrolase substrate

  摘要：

  A gamma -glutamyl tripeptide containing an internally quenched fluorophore has been synthesized and shown to be a substrate for recombinant rat gamma -glutamyl hydrolase. HPLC, LC-MS, and fluorescence spectra support the conclusion that selective hydrolysis occurs at the penultimate peptide bond. Preliminary data indicate that hydrolysis of this substrate can be monitored continuously to yield steady-state kinetic data (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00103-2

文献信息

• The Synthesis of (2<i>S</i>)-4,4-Difluoroglutamyl γ-Peptides Based on Garner’s Aldehyde­ and Fluoro-Reformatsky Chemistry
  作者：James K. Coward、David W. Konas、Jessica J. Pankuch

  DOI：10.1055/s-2002-35616

  日期：——

  development of optically active fluorinated synthetic building blocks of general utility is a current goal of organofluorine chemists. The serine-derived Garner aldehyde was converted to a general 4,4-difluoroamino acid building block via fluoro-Reformatsky reaction with ethyl bromodifluoroacetate. The utility of this building block was demonstrated by the synthesis of derivatives of(2S)-4,4-difluoroglutamine

  开发具有通用性的光学活性氟化合成构件是有机氟化学家当前的目标。丝氨酸衍生的加纳醛通过与溴二氟乙酸乙酯的氟-Reformatsky 反应转化为通用的 4,4-二氟氨基酸结构单元。通过合成 (2S)-4,4-二氟谷氨酰胺、(2S)-4,4-二氟谷氨酸的衍生物并将其掺入设计为机械探针的含荧光团异肽 2 中，证明了该构件的实用性γ-谷氨酰水解酶。化合物 2 被证明是 γ-谷氨酰水解酶的底物，其水解速度明显低于相应的非氟化类似物。
• N-Me-pAB-Glu-γ-Glu-γ-Tyr(3-NO2): an internally quenched fluorogenic γ-glutamyl hydrolase substrate
  作者：Jessica J. Pankuch、James K. Coward

  DOI：10.1016/s0960-894x(01)00103-2

  日期：2001.6

  A gamma -glutamyl tripeptide containing an internally quenched fluorophore has been synthesized and shown to be a substrate for recombinant rat gamma -glutamyl hydrolase. HPLC, LC-MS, and fluorescence spectra support the conclusion that selective hydrolysis occurs at the penultimate peptide bond. Preliminary data indicate that hydrolysis of this substrate can be monitored continuously to yield steady-state kinetic data (C) 2001 Elsevier Science Ltd. All rights reserved.