(S)-2-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionic acid tert-butyl ester | 87362-96-7

• 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: (S)-2-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionic acid tert-butyl ester
• CAS: 87362-96-7
• 化学式: C₂₆H₃₁N₃O₆
• 分子量: 481.549
• InChiKey: FNRVIPOOFZZQNN-BTYIYWSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  136.82
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionic acid tert-butyl ester 在 哌啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 H-N(Tmb)P^MeNA-OtBu
  参考文献：
  名称：

  Stabilization of Type-I .beta.-Turn Conformations in Peptides Containing the NPNA-Repeat Motif of the Plasmodium falciparum Circumsporozoite Protein by Substituting Proline for (S)-.alpha.-Methylproline

  摘要：

  The immunologically dominant central portion of the circumsporozoite (CS) surface protein on the malaria parasite Plasmodium falciparum contains a large number of tandemly repeated NPNA tetrapeptide motifs. The preferred secondary structure of this repeat unit in aqueous solution has been investigated with the aid of the secondary structure-inducing amino acid (S)-alpha-methylproline (p(Me)). H-1-Nuclear magnetic resonance (NMR) and circular dichroism (CD) spectroscopy have been used to probe the structures of synthetic peptides containing one to three tetrapeptide NP(Me)NA units. The far-UV CD spectra of these peptides show more intense negative bands at 215 nm than do similar peptides based on the NPNA motif. This and the temperature dependence of the peptide amide chemical shifts, the pattern of NOE connectivities, and the magnitude of (3)J coupling constants, derived from one- and two-dimensional NMR spectra of Ac(NP(Me)NA)(3)-OH, provide strong evidence for stable turnlike structures. From NOE distance and dihedral angle restraints, structures consistent with the NMR parameters were calculated. These reveal a stable hydrogen-bonded type-I beta-turn conformation (most likely present at 70-80% population) within each NP(Me)NA motif, stabilized by the backbone C-alpha methylation. Side chain to backbone hydrogen bonds involving the side chain amide groups of both asparagine residues also appear to impart stabilization to the turn conformation. No regular repeating conformations were detected in the linker regions connecting each NP(Me)NA unit. Polyclonal antisera raised in rabbits against (NP(Me)NA)(3) recognized intact P. falciparum sporozoites in an immunofluorescence assay as efficiently as antisera raised against (NPNA)(3). This indicates that the type-I beta-turn detected in the P-Me-containing peptide is closely related to the immunologically dominant portion of the folded CS protein. An improved knowledge of the three-dimensional structure of this protein may be of value for the design of second-generation synthetic malaria vaccines.

  DOI：

  10.1021/ja00135a008
• 作为产物：
  描述：

  Fmoc-L-天冬酰胺 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (S)-2-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionic acid tert-butyl ester
  参考文献：
  名称：

  Ynamide 介导的肽键形成：机理研究和合成应用

  摘要：

  Ynamide 偶联剂结合了传统活性酯和偶联剂的优点，同时克服了它们的缺点，并在解决臭名昭著的外消旋/差向异构化问题方面表现出优势。在系统的机理研究的基础上，ynamide 偶联试剂的适用性已成功扩展到肽片段缩合、头尾环化和固相肽合成。

  DOI：

  10.1002/anie.202212247