Fmoc-4-sulfomethyl-Phe(TCE)-OH | 1146758-11-3

• 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: Fmoc-4-sulfomethyl-Phe(TCE)-OH
• 英文别名: L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-[[(2,2,2-trichloroethoxy)sulfonyl]methyl]-；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-(2,2,2-trichloroethoxysulfonylmethyl)phenyl]propanoic acid
• CAS: 1146758-11-3
• 化学式: C₂₇H₂₄Cl₃NO₇S
• 分子量: 612.915
• InChiKey: QXNUQPLTPOHMHT-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Fmoc-4-sulfomethyl-Phe(TCE)-OH 在 甲酸铵 、 锌 作用下， 以 甲醇 为溶剂， 以94%的产率得到N-[(9H-芴-9-基甲氧基)羰基]-4-(磺基甲基)-L-苯丙氨酸
  参考文献：
  名称：

  Trichloroethyl Group As a Protecting Group for Sulfonates and Its Application to the Synthesis of a Disulfonate Analog of the Tyrosine Sulfated PSGL-1₄₃₋₅₀ Peptide

  摘要：

  The trichloroethyl (TCE) group is shown to be a viable protecting group for sulfonates. TCE-protected sulfonates were found to be particularly stable to acid, a key characteristic that led to a straightforward enantioselective synthesis of L-FmocPhe(p-CH2SO3TCE)OH. This was used as a building block for the solid phase synthesis of an octapeptide corresponding to P-selectin glycoprotein ligand-1 residues 43-50 (PSGL-1(43-50)) in which sulfotyrosine residues 46 and 48 were replaced with (sulfonomethyl)phenylalanine (SmP), an important hydrolytically stable sulfotyrosine mimic.

  DOI：

  10.1021/jo900122c
• 作为产物：
  描述：

  (2S)-2-amino-3-[4-(2,2,2-trichloroethoxysulfonylmethyl)phenyl]propanoic acid 、 氯甲酸-9-芴基甲酯 在 sodium carbonate 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.0h， 以85%的产率得到Fmoc-4-sulfomethyl-Phe(TCE)-OH
  参考文献：
  名称：

  Trichloroethyl Group As a Protecting Group for Sulfonates and Its Application to the Synthesis of a Disulfonate Analog of the Tyrosine Sulfated PSGL-1₄₃₋₅₀ Peptide

  摘要：

  The trichloroethyl (TCE) group is shown to be a viable protecting group for sulfonates. TCE-protected sulfonates were found to be particularly stable to acid, a key characteristic that led to a straightforward enantioselective synthesis of L-FmocPhe(p-CH2SO3TCE)OH. This was used as a building block for the solid phase synthesis of an octapeptide corresponding to P-selectin glycoprotein ligand-1 residues 43-50 (PSGL-1(43-50)) in which sulfotyrosine residues 46 and 48 were replaced with (sulfonomethyl)phenylalanine (SmP), an important hydrolytically stable sulfotyrosine mimic.

  DOI：

  10.1021/jo900122c

文献信息

• Trichloroethyl Group As a Protecting Group for Sulfonates and Its Application to the Synthesis of a Disulfonate Analog of the Tyrosine Sulfated PSGL-1₄₃₋₅₀ Peptide
  作者：Ahmed M. Ali、Bryan Hill、Scott D. Taylor

  DOI：10.1021/jo900122c

  日期：2009.5.1

  The trichloroethyl (TCE) group is shown to be a viable protecting group for sulfonates. TCE-protected sulfonates were found to be particularly stable to acid, a key characteristic that led to a straightforward enantioselective synthesis of L-FmocPhe(p-CH2SO3TCE)OH. This was used as a building block for the solid phase synthesis of an octapeptide corresponding to P-selectin glycoprotein ligand-1 residues 43-50 (PSGL-1(43-50)) in which sulfotyrosine residues 46 and 48 were replaced with (sulfonomethyl)phenylalanine (SmP), an important hydrolytically stable sulfotyrosine mimic.