N-[(9H-芴-9-基甲氧基)羰基]-4-(磺基甲基)-L-苯丙氨酸 | 206060-45-9

• 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
• 中文名称: N-[(9H-芴-9-基甲氧基)羰基]-4-(磺基甲基)-L-苯丙氨酸
• 中文别名: N-FMOC-L-4-磺甲基苯丙氨酸
• 英文名称: N-(fluorenyl-9-methoxycarbonyl)-L-(p-sulfomethyl)phenylalanine
• 英文别名: FmocPhe(p-CH2SO3H)OH；FmocTYSN；L-Phenylalanine,N-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-(sulfomethyl)-；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-(sulfomethyl)phenyl]propanoic acid
• CAS: 206060-45-9
• 化学式: C₂₅H₂₃NO₇S
• 分子量: 481.526
• InChiKey: VJJJONZWAYIHQW-QHCPKHFHSA-N

物化性质

• 熔点：
  >270 °C
• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(9H-芴-9-基甲氧基)羰基]-4-(磺基甲基)-L-苯丙氨酸 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-(fluorenyl-9-methoxycarboynl)-L-(p-sulfomethyl)phenylalanyl-L-(4-O-benzyl)-aspartic acid
  参考文献：
  名称：

  (p-Sulfomethyl)phenylalanine as a mimic of O-sulfatyl-tyrosine in synthetic partial sequences of P-Selectin glycoprotein ligand 1 (PSGL-1)

  摘要：

  Fmoc-L-(p-sulfomethyl)phenylalanine, a bioisosteric mimic of acid-sensitive O-sulfatyl tyrosine, was synthesized from L-tyrosine according to a novel route. Partial sequences of the recognition site of P-Selectin glycoprotein ligand 1 (PSGL-1), which contain (sulfomethyl) phenylalanine were synthesized on solid-phase. By fragment condensation, a sialyl Lewis(x) peptide conjugate containing a (sulfomethyl)phenylalanine mimic of O-sulfatyl tyrosine was prepared without destruction of the acid-sensitive fucoside bond within the saccharide side chain. Compounds of this type are of interest as sufficiently acid-stable potential inhibitors of P-Selectin in inflammatory processes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.028
• 作为产物：
  描述：

  (S)-甲基2-((叔-丁氧羰基)氨基)-3-(4-氰基苯基)丙酯 在 镍 盐酸 、 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 水 、 氢气 、 sodium carbonate 、 三乙胺 、 三苯基膦 、 sodium sulfite 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 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：

  (p-Sulfomethyl)phenylalanine as a mimic of O-sulfatyl-tyrosine in synthetic partial sequences of P-Selectin glycoprotein ligand 1 (PSGL-1)

  摘要：

  Fmoc-L-(p-sulfomethyl)phenylalanine, a bioisosteric mimic of acid-sensitive O-sulfatyl tyrosine, was synthesized from L-tyrosine according to a novel route. Partial sequences of the recognition site of P-Selectin glycoprotein ligand 1 (PSGL-1), which contain (sulfomethyl) phenylalanine were synthesized on solid-phase. By fragment condensation, a sialyl Lewis(x) peptide conjugate containing a (sulfomethyl)phenylalanine mimic of O-sulfatyl tyrosine was prepared without destruction of the acid-sensitive fucoside bond within the saccharide side chain. Compounds of this type are of interest as sufficiently acid-stable potential inhibitors of P-Selectin in inflammatory processes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.028

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.
• (p-Sulfomethyl)phenylalanine as a mimic of O-sulfatyl-tyrosine in synthetic partial sequences of P-Selectin glycoprotein ligand 1 (PSGL-1)
  作者：Holger Herzner、Horst Kunz

  DOI：10.1016/j.tet.2007.03.028

  日期：2007.7

  Fmoc-L-(p-sulfomethyl)phenylalanine, a bioisosteric mimic of acid-sensitive O-sulfatyl tyrosine, was synthesized from L-tyrosine according to a novel route. Partial sequences of the recognition site of P-Selectin glycoprotein ligand 1 (PSGL-1), which contain (sulfomethyl) phenylalanine were synthesized on solid-phase. By fragment condensation, a sialyl Lewis(x) peptide conjugate containing a (sulfomethyl)phenylalanine mimic of O-sulfatyl tyrosine was prepared without destruction of the acid-sensitive fucoside bond within the saccharide side chain. Compounds of this type are of interest as sufficiently acid-stable potential inhibitors of P-Selectin in inflammatory processes. (c) 2007 Elsevier Ltd. All rights reserved.