H-Ile-Phe-Ser(tBu)-Pro-Ile-Pro-OtBu | 1025798-99-5

• 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: H-Ile-Phe-Ser(tBu)-Pro-Ile-Pro-OtBu
• 英文别名: tert-butyl (2S)-1-[(2S,3S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S,3S)-2-amino-3-methylpentanoyl]amino]-3-phenylpropanoyl]amino]-3-[(2-methylpropan-2-yl)oxy]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylpentanoyl]pyrrolidine-2-carboxylate
• CAS: 1025798-99-5
• 化学式: C₄₂H₆₈N₆O₈
• 分子量: 785.037
• InChiKey: FCEKPAGHZXQRAP-DVFLVHSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  56
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  190
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  H-Ile-Phe-Ser(tBu)-Pro-Ile-Pro-OtBu 在 氰基磷酸二乙酯 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 二乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成 stylopeptide 1
  参考文献：
  名称：

  Synthesis of the Marine Sponge Cycloheptapeptide Stylopeptide 1¹

  摘要：

  The solution-phase synthesis of the marine sponge stylopeptide 1 (2), cyclo-(Leu-Ile-Phe-Ser-Pro-Ile-Pro), was conveniently accomplished using N-terminal Fmoc- and C-terminal tert-butyl ester protection with tert-butyl ether side-chain blocking for serine. Peptide bond formation for each step except for the final cyclization was effected with diethyl phosphorocyanidate to give the linear heptapeptide in 19% yield. Both TBTU (4) or BOP-Cl (5) were used to cyclize the heptapeptide and resulted in 67% and 13% yields of stylopeptide 1 (2), respectively. Peptide 2 was obtained in 11% overall yield based on the TBTU cyclization procedure. The general approach represents a useful improvement in the synthesis of such cyclic peptides. The synthetic stylopeptide 1 (2) proved to be identical with the natural product.

  DOI：

  10.1021/jo951986b
• 作为产物：
  描述：

  N-Fmoc-Ile-Phe-Ser(Bu^t)-Pro-Ile-Pro-OBu^t 在 二乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 H-Ile-Phe-Ser(tBu)-Pro-Ile-Pro-OtBu
  参考文献：
  名称：

  Synthesis of the Marine Sponge Cycloheptapeptide Stylopeptide 1¹

  摘要：

  The solution-phase synthesis of the marine sponge stylopeptide 1 (2), cyclo-(Leu-Ile-Phe-Ser-Pro-Ile-Pro), was conveniently accomplished using N-terminal Fmoc- and C-terminal tert-butyl ester protection with tert-butyl ether side-chain blocking for serine. Peptide bond formation for each step except for the final cyclization was effected with diethyl phosphorocyanidate to give the linear heptapeptide in 19% yield. Both TBTU (4) or BOP-Cl (5) were used to cyclize the heptapeptide and resulted in 67% and 13% yields of stylopeptide 1 (2), respectively. Peptide 2 was obtained in 11% overall yield based on the TBTU cyclization procedure. The general approach represents a useful improvement in the synthesis of such cyclic peptides. The synthetic stylopeptide 1 (2) proved to be identical with the natural product.

  DOI：

  10.1021/jo951986b

文献信息

• Synthesis of the Marine Sponge Cycloheptapeptide Stylopeptide 1¹
  作者：George R. Pettit、Stuart R. Taylor

  DOI：10.1021/jo951986b

  日期：1996.1.1

  The solution-phase synthesis of the marine sponge stylopeptide 1 (2), cyclo-(Leu-Ile-Phe-Ser-Pro-Ile-Pro), was conveniently accomplished using N-terminal Fmoc- and C-terminal tert-butyl ester protection with tert-butyl ether side-chain blocking for serine. Peptide bond formation for each step except for the final cyclization was effected with diethyl phosphorocyanidate to give the linear heptapeptide in 19% yield. Both TBTU (4) or BOP-Cl (5) were used to cyclize the heptapeptide and resulted in 67% and 13% yields of stylopeptide 1 (2), respectively. Peptide 2 was obtained in 11% overall yield based on the TBTU cyclization procedure. The general approach represents a useful improvement in the synthesis of such cyclic peptides. The synthetic stylopeptide 1 (2) proved to be identical with the natural product.