N-(fluorenyl-9-methoxycarbonyl)-L-(p-sulfomethyl)phenylalanine methyl ester | 945245-47-6

• 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-(fluorenyl-9-methoxycarbonyl)-L-(p-sulfomethyl)phenylalanine methyl ester
• CAS: 945245-47-6
• 化学式: C₂₆H₂₅NO₇S
• 分子量: 495.553
• InChiKey: QYJURDKQZMQFIZ-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  119.0
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(fluorenyl-9-methoxycarbonyl)-L-(p-sulfomethyl)phenylalanine methyl ester 在 sodium hydroxide 、 N,N-二异丙基乙胺 、 三氟乙酸 、 subtilisin 作用下， 以 phosphate buffer 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 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：

  N-(fluorenyl-9-methoxycarbonyl)-L-(p-hydroxymethyl)phenylalanine methyl ester 在 N-溴代丁二酰亚胺(NBS) 、 水 、 三苯基膦 、 sodium sulfite 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 N-(fluorenyl-9-methoxycarbonyl)-L-(p-sulfomethyl)phenylalanine methyl ester
  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