cyclo[Arg(Pmc)(Pmc)-Gly-Asp(OtBu)(OtBu)-D-Phe-Lys(Boc)] | 941276-40-0

• 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: cyclo[Arg(Pmc)(Pmc)-Gly-Asp(OtBu)(OtBu)-D-Phe-Lys(Boc)]
• 英文别名: tert-butyl 2-[(2S,5R,8S,11S)-11-[3-[[amino-[(2,2,5,7,8-pentamethyl-3,4-dihydrochromen-6-yl)sulfonylamino]methylidene]amino]propyl]-5-benzyl-8-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentazacyclopentadec-2-yl]acetate
• CAS: 941276-40-0
• 化学式: C₅₀H₇₅N₉O₁₂S
• 分子量: 1026.26
• InChiKey: FLLUMPGAPHTRPU-FBBJYXRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  72
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  312
• 氢给体数：
  8
• 氢受体数：
  13

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  NΑ-FMOC-NΩ-(2,2,5,7,8-五甲基苯并二氢吡喃-6-磺酰基)-L-精氨酸	Fmoc-Arg(Pbf)-OH	119831-72-0	C35H42N4O7S	662.807

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 cyclo[Arg(Pmc)(Pmc)-Gly-Asp(OtBu)(OtBu)-D-Phe-Lys(Boc)] 以 水 为溶剂， 以82%的产率得到cRGDfK*2TFA
  参考文献：
  名称：

  An improved synthesis of a selective αvβ3-integrin antagonist cyclo(-RGDfK-)

  摘要：

  The cyclic pentapeptide cyclo(-Arg-Gly-Asp-D-Phe-Lys-) is a highly potent and selective inhibitor for the alpha(v)beta(3) integrin. A related compound, cyclo(-Arg-Gly-Asp-D-Phe-Val-), is a promising anticancer drug candidate; it inhibits angiogenesis and induces apoptosis in vascular cells. We have developed an improved solid-phase synthesis based on Kessler's procedure to afford cyclo(-RGDfK-) peptide in high purity and high yield in a multi-gram scale. This improved synthesis is environmentally friendly and may be generally applicable to other related cyclic peptide syntheses. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01060-1
• 作为产物：
  描述：

  HO-Gly-Arg(Pbf)-Lys(Boc)-D-Phe-Asp(OtBu)-NH2*HOAc 在 4-二甲氨基吡啶 、 1-丙基磷酸酐 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 cyclo[Arg(Pmc)(Pmc)-Gly-Asp(OtBu)(OtBu)-D-Phe-Lys(Boc)]
  参考文献：
  名称：

  An improved synthesis of a selective αvβ3-integrin antagonist cyclo(-RGDfK-)

  摘要：

  The cyclic pentapeptide cyclo(-Arg-Gly-Asp-D-Phe-Lys-) is a highly potent and selective inhibitor for the alpha(v)beta(3) integrin. A related compound, cyclo(-Arg-Gly-Asp-D-Phe-Val-), is a promising anticancer drug candidate; it inhibits angiogenesis and induces apoptosis in vascular cells. We have developed an improved solid-phase synthesis based on Kessler's procedure to afford cyclo(-RGDfK-) peptide in high purity and high yield in a multi-gram scale. This improved synthesis is environmentally friendly and may be generally applicable to other related cyclic peptide syntheses. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01060-1