Fmoc-(Pro)5-Amp[Fmoc-(Pro)5]-OH | 452308-69-9

• 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: Fmoc-(Pro)5-Amp[Fmoc-(Pro)5]-OH
• 英文别名: Fmoc-Pro5-L-Amp(Fmoc-Pro5)-OH；(2S,4S)-1-[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]-4-[[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]pyrrolidine-2-carboxylic acid
• CAS: 452308-69-9
• 化学式: C₈₅H₁₀₀N₁₂O₁₆
• 分子量: 1545.8
• InChiKey: SGKOKUBNAVAGFS-YCIMIBOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  113
• 可旋转键数：
  18
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  308
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  Fmoc-(Pro)5-Amp[Fmoc-(Pro)5]-OH 、 alkaline earth salt of/the/ methylsulfuric acid 生成 Fmoc-Pro5-L-Amp(Fmoc-Pro5)-Pro6-OH
  参考文献：
  名称：

  Branched Poly(proline) Peptides: An Efficient New Approach to the Synthesis of Repetitive Branched Peptides

  摘要：

  Proline is unique among the twenty genetically coded amino acids in that it contains both a cyclic backbone and a secondary alpha-amino group, These structural features impart unique stereochemical properties on proline. Poly(proline) oligomers exist in two distinct conformations in solution. In organic solvents they tend to adopt a conformation known as poly(proline) I (PPI), whereas in aqueous solvents they tend to adopt a different conformation known as poly(proline) II (PPII). We report here a new family of branched poly(proline) peptides. After a careful study of the different approaches, an efficient protocol for the synthesis of this kind of peptide has been established. cis-4-Amino-L-proline was mainly used as a branching unit in order to minimize its effects on the conformation of the rest of the molecule. The synthetic strategy employed was based on a convergent solid-phase peptide synthesis methodology that gave crude peptides that were easy to purify. This approach provides a new method for the synthesis of other repetitive branched peptides, minimizing not only synthetic difficulties but also purification problems. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200206)2002:11<1756::aid-ejoc1756>3.0.co;2-a
• 作为产物：
  描述：

  BOC-L-脯氨酸 、 Fmoc-L-脯氨酸 、 N-Boc-顺式-4-Fmoc-氨基-L-脯氨酸 生成 Fmoc-(Pro)5-Amp[Fmoc-(Pro)5]-OH
  参考文献：
  名称：

  基于聚脯氨酸螺旋的肽树状聚合物

  摘要：

  我们提出了一个基于聚脯氨酸螺旋和 cis-4-amino-L-proline 作为分支单位的新肽树枝状聚合物家族。树枝状聚合物是通过收敛固相肽合成方法合成的。聚脯氨酸 I 型螺旋和聚脯氨酸 II 型螺旋之间的构象转变是通过圆二色性观察到的具有超过 14 个脯氨酸残基的支链聚脯氨酸结构单元和由此产生的树枝状聚合物。发现线性和树突状聚脯氨酸都被大鼠肾细胞积极内化。初步结果表明，抗生素环丙沙星在 99.5% 丙醇中与支链聚脯氨酸形成复合物。

  DOI：

  10.1021/ja020364m

文献信息

• Peptide Dendrimers Based on Polyproline Helices
  作者：Laia Crespo、Glòria Sanclimens、Beatriz Montaner、Ricardo Pérez-Tomás、Miriam Royo、Miquel Pons、Fernando Albericio、Ernest Giralt

  DOI：10.1021/ja020364m

  日期：2002.7.1

  We present a new family of peptide dendrimers based on polyproline helices and cis-4-amino-L-proline as a branching unit. Dendrimers were synthesized by a convergent solid-phase peptide synthesis approach. The conformational transition between polyproline type I helix and polyproline type II helix was observed by circular dichroism in branched polyproline building blocks with more than 14 proline residues

  我们提出了一个基于聚脯氨酸螺旋和 cis-4-amino-L-proline 作为分支单位的新肽树枝状聚合物家族。树枝状聚合物是通过收敛固相肽合成方法合成的。聚脯氨酸 I 型螺旋和聚脯氨酸 II 型螺旋之间的构象转变是通过圆二色性观察到的具有超过 14 个脯氨酸残基的支链聚脯氨酸结构单元和由此产生的树枝状聚合物。发现线性和树突状聚脯氨酸都被大鼠肾细胞积极内化。初步结果表明，抗生素环丙沙星在 99.5% 丙醇中与支链聚脯氨酸形成复合物。
• Branched Poly(proline) Peptides: An Efficient New Approach to the Synthesis of Repetitive Branched Peptides
  作者：Laia Crespo、Glòria Sanclimens、Miriam Royo、Ernest Giralt、Fernando Albericio

  DOI：10.1002/1099-0690(200206)2002:11<1756::aid-ejoc1756>3.0.co;2-a

  日期：2002.6

  Proline is unique among the twenty genetically coded amino acids in that it contains both a cyclic backbone and a secondary alpha-amino group, These structural features impart unique stereochemical properties on proline. Poly(proline) oligomers exist in two distinct conformations in solution. In organic solvents they tend to adopt a conformation known as poly(proline) I (PPI), whereas in aqueous solvents they tend to adopt a different conformation known as poly(proline) II (PPII). We report here a new family of branched poly(proline) peptides. After a careful study of the different approaches, an efficient protocol for the synthesis of this kind of peptide has been established. cis-4-Amino-L-proline was mainly used as a branching unit in order to minimize its effects on the conformation of the rest of the molecule. The synthetic strategy employed was based on a convergent solid-phase peptide synthesis methodology that gave crude peptides that were easy to purify. This approach provides a new method for the synthesis of other repetitive branched peptides, minimizing not only synthetic difficulties but also purification problems. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.