N-Fmoc-Tyr(OBu^t)-Pro-Phe-Pro-OBu^t | 221689-40-3

• 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-Fmoc-Tyr(OBu^t)-Pro-Phe-Pro-OBu^t
• 英文别名: Fmoc-Tyr(tBu)-Pro-Phe-Pro-OtBu；tert-butyl (2S)-1-[(2S)-2-[[(2S)-1-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]pyrrolidine-2-carboxylate
• CAS: 221689-40-3
• 化学式: C₅₁H₆₀N₄O₈
• 分子量: 857.059
• InChiKey: VTBPRROGRXHEMV-ITMZJIMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  63
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-Fmoc-Tyr(OBu^t)-Pro-Phe-Pro-OBu^t 在 N-羟基-7-氮杂苯并三氮唑 、 三(2-氨基乙基)胺 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tet 、 ramethyluronium tetrafluoroborate 、 sopropylethylamine 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 phakellistatin 2
  参考文献：
  名称：

  Antineoplastic Agents. 400. Synthesis of the Indian Ocean Marine Sponge Cyclic Heptapeptide Phakellistatin 2^,1a

  摘要：

  Solution-phase synthesis of the marine sponge constituent phakellistatin 2 (1), cyclo(Tyr-Pro-Phe-Prone-Ile-Pro), was completed using a combination of stepwise coupling and (4 + 3) segment condensation. Use of diethyl phosphorocyanidate for the peptide bond formations gave the linear heptapeptide in 54% yield. Cyclization was achieved in high yields utilizing TBTU (2), BOP-C1 (3), PyBroP (4), and HOAt (5), resulting in 50-65% yields of phakellistatin 2 (1) depending on the method employed. The synthetic cyclic peptide was chemically but not biologically identical with the natural product.

  DOI：

  10.1021/np980168m
• 作为产物：
  描述：

  (9H-fluoren-9-yl)methyl tert-butylpyrrolidine-1,2-dicarboxylate 在 三(2-氨基乙基)胺 、 氰基磷酸二乙酯 、 N,N-二异丙基乙胺 作用下， 生成 N-Fmoc-Tyr(OBu^t)-Pro-Phe-Pro-OBu^t
  参考文献：
  名称：

  Antineoplastic Agents. 400. Synthesis of the Indian Ocean Marine Sponge Cyclic Heptapeptide Phakellistatin 2^,1a

  摘要：

  Solution-phase synthesis of the marine sponge constituent phakellistatin 2 (1), cyclo(Tyr-Pro-Phe-Prone-Ile-Pro), was completed using a combination of stepwise coupling and (4 + 3) segment condensation. Use of diethyl phosphorocyanidate for the peptide bond formations gave the linear heptapeptide in 54% yield. Cyclization was achieved in high yields utilizing TBTU (2), BOP-C1 (3), PyBroP (4), and HOAt (5), resulting in 50-65% yields of phakellistatin 2 (1) depending on the method employed. The synthetic cyclic peptide was chemically but not biologically identical with the natural product.

  DOI：

  10.1021/np980168m

文献信息

• Antineoplastic Agents. 400. Synthesis of the Indian Ocean Marine Sponge Cyclic Heptapeptide Phakellistatin 2^,1a
  作者：George R. Pettit、Monte R. Rhodes、Rui Tan

  DOI：10.1021/np980168m

  日期：1999.3.1

  Solution-phase synthesis of the marine sponge constituent phakellistatin 2 (1), cyclo(Tyr-Pro-Phe-Prone-Ile-Pro), was completed using a combination of stepwise coupling and (4 + 3) segment condensation. Use of diethyl phosphorocyanidate for the peptide bond formations gave the linear heptapeptide in 54% yield. Cyclization was achieved in high yields utilizing TBTU (2), BOP-C1 (3), PyBroP (4), and HOAt (5), resulting in 50-65% yields of phakellistatin 2 (1) depending on the method employed. The synthetic cyclic peptide was chemically but not biologically identical with the natural product.