(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-[1-hydroxy-2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]phenyl]propanoic acid | 543720-21-4

• 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: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-[1-hydroxy-2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]phenyl]propanoic acid
• CAS: 543720-21-4
• 化学式: C₃₀H₃₁NO₇
• 分子量: 517.579
• InChiKey: MUBJWQGTLLLBGE-PMCHYTPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-[1-hydroxy-2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]phenyl]propanoic acid 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoacetyl]phenyl]propanoic acid
  参考文献：
  名称：

  Peptidic α-Ketocarboxylic Acids and Sulfonamides as Inhibitors of Protein Tyrosine Phosphatases

  摘要：

  One common approach for designing protein tyrosine phosphatase (PTPase) inhibitors is to incorporate a nonhydrolyzable phosphotyrosine (pTyr) mimic into a peptide substrate for PTPases. This report describes the synthesis of three such nonhydrolyzable pTyr mimics that contain alpha-ketoacid, alpha-hydroxyacid, and methylenesulfonamide functional groups in place of the phosphate. These pTyr mimics were incorporated into the peptide sequence Ac-Asp-Ala-Asp-Glu-X-Leu-NH2, where X is the pTyr mimic, and analyzed for activity against the Yersinia PTPase and PTP1B.

  DOI：

  10.1021/jo034113n
• 作为产物：
  描述：

  α-(4-methylphenyl)-α-oxoacetic acid tert-butyl ester 在 palladium dihydroxide N-溴代丁二酰亚胺(NBS) 、 氢气 、 碳酸氢钠 、 lithium hexamethyldisilazane 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 四氯化碳 、 六甲基磷酰三胺 、 水 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 7.67h， 生成 (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-[1-hydroxy-2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]phenyl]propanoic acid
  参考文献：
  名称：

  Peptidic α-Ketocarboxylic Acids and Sulfonamides as Inhibitors of Protein Tyrosine Phosphatases

  摘要：

  One common approach for designing protein tyrosine phosphatase (PTPase) inhibitors is to incorporate a nonhydrolyzable phosphotyrosine (pTyr) mimic into a peptide substrate for PTPases. This report describes the synthesis of three such nonhydrolyzable pTyr mimics that contain alpha-ketoacid, alpha-hydroxyacid, and methylenesulfonamide functional groups in place of the phosphate. These pTyr mimics were incorporated into the peptide sequence Ac-Asp-Ala-Asp-Glu-X-Leu-NH2, where X is the pTyr mimic, and analyzed for activity against the Yersinia PTPase and PTP1B.

  DOI：

  10.1021/jo034113n

文献信息

• Peptidic α-Ketocarboxylic Acids and Sulfonamides as Inhibitors of Protein Tyrosine Phosphatases
  作者：Yen Ting Chen、Jian Xie、Christopher T. Seto

  DOI：10.1021/jo034113n

  日期：2003.5.1

  One common approach for designing protein tyrosine phosphatase (PTPase) inhibitors is to incorporate a nonhydrolyzable phosphotyrosine (pTyr) mimic into a peptide substrate for PTPases. This report describes the synthesis of three such nonhydrolyzable pTyr mimics that contain alpha-ketoacid, alpha-hydroxyacid, and methylenesulfonamide functional groups in place of the phosphate. These pTyr mimics were incorporated into the peptide sequence Ac-Asp-Ala-Asp-Glu-X-Leu-NH2, where X is the pTyr mimic, and analyzed for activity against the Yersinia PTPase and PTP1B.