N-phenylmethoxycarbonylglutathione | 4909-66-4

• 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-phenylmethoxycarbonylglutathione
• 英文别名: N-[N-(N-benzyloxycarbonyl-γ-L-glutamyl)-L-cysteinyl]-glycine；N-[N-(N-Benzyloxycarbonyl-γ-L-glutamyl)-L-cysteinyl]-glycin；Cbz-gGlu-Cys-Gly-OH；(2S)-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxo-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 4909-66-4
• 化学式: C₁₈H₂₃N₃O₈S
• 分子量: 441.462
• InChiKey: DOVWPKZUJKQEEA-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  172
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-phenylmethoxycarbonylglutathione 、 dimethyl (3S)-2-azido-3-hydroxysuccinate 在 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以35%的产率得到
  参考文献：
  名称：

  Synthesis of azide derivative and discovery of glyoxalase pathway inhibitor against pathogenic bacteria

  摘要：

  A glyoxalase inhibitor was synthesized and tested against Staphylococcus aureus for first time and showed MIC90 of 20 mu g/ml. Henceforth, we synthesized unnatural azide derivative of the same inhibitor to improve the biological activity. In that order, an azide carboxylate was synthesized from dimethyl tartrate by tosylation and azide substitution. The synthesized, azide compound was coupled with glutathione derivative in high yield and tested against S. aureus and showed improved MIC90 of 5 mu g/ml. In general, it can be also easily converted to unnatural beta-amino acid in good yield. The shown methodology will be extended to study induced suicide in Burkholderia mallei, Francisella tularensis and Mycobacterium tuberculosis in future. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.011
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 1,4-二氧六环 、 sodium hydroxide 作用下， 生成 N-phenylmethoxycarbonylglutathione
  参考文献：
  名称：

  Harington; Mead, Biochemical Journal, 1935, vol. 29, p. 1602,1605

  摘要：

  DOI：

文献信息

• Harington; Mead, Biochemical Journal, 1935, vol. 29, p. 1602,1605
  作者：Harington、Mead

  DOI：——

  日期：——
• Synthesis of azide derivative and discovery of glyoxalase pathway inhibitor against pathogenic bacteria
  作者：Benson Edagwa、Yiran Wang、Prabagaran Narayanasamy

  DOI：10.1016/j.bmcl.2013.09.011

  日期：2013.11

  A glyoxalase inhibitor was synthesized and tested against Staphylococcus aureus for first time and showed MIC90 of 20 mu g/ml. Henceforth, we synthesized unnatural azide derivative of the same inhibitor to improve the biological activity. In that order, an azide carboxylate was synthesized from dimethyl tartrate by tosylation and azide substitution. The synthesized, azide compound was coupled with glutathione derivative in high yield and tested against S. aureus and showed improved MIC90 of 5 mu g/ml. In general, it can be also easily converted to unnatural beta-amino acid in good yield. The shown methodology will be extended to study induced suicide in Burkholderia mallei, Francisella tularensis and Mycobacterium tuberculosis in future. (c) 2013 Elsevier Ltd. All rights reserved.