2-((3S,9S,13S,18R)-9-(3-guanidinopropyl)-2,5,8,11-tetraoxo-13,18-diphenyl-1,4,7,10-tetraazacyclononadec-15-en-3-yl)acetic acid | 1458609-53-4

• 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: 2-((3S,9S,13S,18R)-9-(3-guanidinopropyl)-2,5,8,11-tetraoxo-13,18-diphenyl-1,4,7,10-tetraazacyclononadec-15-en-3-yl)acetic acid
• CAS: 1458609-53-4
• 化学式: C₃₃H₄₃N₇O₆
• 分子量: 633.748
• InChiKey: JPKNUDOCNLXWFJ-FWEHEUNISA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  215.6
• 氢给体数：
  8.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-((3S,9S,13S,18R)-9-(3-guanidinopropyl)-2,5,8,11-tetraoxo-13,18-diphenyl-1,4,7,10-tetraazacyclononadec-15-en-3-yl)acetic acid 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 以4%的产率得到2-[(3S,9S,13S,18R)-9-[3-(diaminomethylideneamino)propyl]-2,5,8,11-tetraoxo-13,18-diphenyl-1,4,7,10-tetrazacyclononadec-3-yl]acetic acid
  参考文献：
  名称：

  Synthesis of a macrocycle based on Linked Amino Acid Mimetics (LAAM)

  摘要：

  We report the synthesis of a macrocycle utilizing a novel framework of standard amino acids in combination with subunits that we have named as Linked Amino Acid Mimetics (LAAMs). Macrocycles based on the LAAM concept provide both a peptide targeting region and two independently variable functional regions. In the prototype structure, the commonly known Arg-Gly-Asp (RGD) sequence was used for the targeting region. The functional regions contain a phenyl group, and the linkage was formed via a Ring-Closing Metathesis (RCM) reaction. (c) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.08.041
• 作为产物：
  描述：

  Fmoc-Asp(OAll)-Pol 、 Fmoc-甘氨酸 、 (R)-2-phenylpent-4-en-1-amine hydrochloride 、 Fmoc-Pbf-L-精氨酸 、 (S)-3-phenylhex-5-enoic acid 在 哌啶 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 1.12h， 生成 2-((3S,9S,13S,18R)-9-(3-guanidinopropyl)-2,5,8,11-tetraoxo-13,18-diphenyl-1,4,7,10-tetraazacyclononadec-15-en-3-yl)acetic acid
  参考文献：
  名称：

  Synthesis of a macrocycle based on Linked Amino Acid Mimetics (LAAM)

  摘要：

  We report the synthesis of a macrocycle utilizing a novel framework of standard amino acids in combination with subunits that we have named as Linked Amino Acid Mimetics (LAAMs). Macrocycles based on the LAAM concept provide both a peptide targeting region and two independently variable functional regions. In the prototype structure, the commonly known Arg-Gly-Asp (RGD) sequence was used for the targeting region. The functional regions contain a phenyl group, and the linkage was formed via a Ring-Closing Metathesis (RCM) reaction. (c) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.08.041