2(R)-{4-[(9H-fluoren-9-ylmethoxycarbonylamino)-methyl]-[1,2,3]triazol-1yl}-4-methyl-pentanoic acid | 583871-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2(R)-{4-[(9H-fluoren-9-ylmethoxycarbonylamino)-methyl]-[1,2,3]triazol-1yl}-4-methyl-pentanoic acid
• 英文别名: (2R)-2-[4-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]triazol-1-yl]-4-methylpentanoic acid
• CAS: 583871-74-3
• 化学式: C₂₄H₂₆N₄O₄
• 分子量: 434.495
• InChiKey: FJMQXRAPURVGDD-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2(R)-{4-[(9H-fluoren-9-ylmethoxycarbonylamino)-methyl]-[1,2,3]triazol-1yl}-4-methyl-pentanoic acid 在 N-羟基-7-氮杂苯并三氮唑 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (2R,5S,13R,16S)-5,16-Dibenzyl-2,13-diisobutyl-1,4,7,10,11,12,15,18,21,22-decaaza-tricyclo[18.2.1.1^9,12]tetracosa-9(24),10,20(23),21-tetraene-3,6,14,17-tetraone
  参考文献：
  名称：

  A Heterocyclic Peptide Nanotube

  摘要：

  An open-ended hollow tubular structure is designed based on hydrogen-bond-directed self-assembly of a chimeric cyclic peptide subunit comprised of alternating alpha- and is an element of-amino acids. The design features a novel 1,4-disubstituted-1,2,3-triazole 6-amino acid and its utility as a peptide backbone substitute. The N-Fmoc-protected is an element of-amino acid was synthesized in high yield and optical purity in three steps from readily available starting materials and was employed in solid-phase peptide synthesis to afford the desired cyclic peptide structure. The cyclic peptide self-assembly has been studied in solution by H-1 NMR and mass spectrometry and the resulting tubular ensemble characterized in the solid state by X-ray crystallography.

  DOI：

  10.1021/ja034358h
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 2,6-二甲基吡啶 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 3.0h， 生成 2(R)-{4-[(9H-fluoren-9-ylmethoxycarbonylamino)-methyl]-[1,2,3]triazol-1yl}-4-methyl-pentanoic acid
  参考文献：
  名称：

  A Heterocyclic Peptide Nanotube

  摘要：

  An open-ended hollow tubular structure is designed based on hydrogen-bond-directed self-assembly of a chimeric cyclic peptide subunit comprised of alternating alpha- and is an element of-amino acids. The design features a novel 1,4-disubstituted-1,2,3-triazole 6-amino acid and its utility as a peptide backbone substitute. The N-Fmoc-protected is an element of-amino acid was synthesized in high yield and optical purity in three steps from readily available starting materials and was employed in solid-phase peptide synthesis to afford the desired cyclic peptide structure. The cyclic peptide self-assembly has been studied in solution by H-1 NMR and mass spectrometry and the resulting tubular ensemble characterized in the solid state by X-ray crystallography.

  DOI：

  10.1021/ja034358h

文献信息

• [EN] TRIAZOLE ϵ-AMINO ACIDS<br/>[FR] ACIDES AMINO TRIAZOLE- DOLLAR G(E)
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2005007675A2

  公开（公告）日：2005-01-27

  The invention provides 1,2,3-triazole ϵ-amino acids as well as peptides and polypeptides having at least one 1,2,3-­triazole ϵ-amino acid. The peptides of the invention can be linear or cyclic. In some embodiments, the cyclic peptides of the invention can assemble into supramolecular structures that can be used be used therapeutically or for small molecule transport and the modulation of small molecule transport within and between cells.
• A Heterocyclic Peptide Nanotube
  作者：W. Seth Horne、C. David Stout、M. Reza Ghadiri

  DOI：10.1021/ja034358h

  日期：2003.8.1

  An open-ended hollow tubular structure is designed based on hydrogen-bond-directed self-assembly of a chimeric cyclic peptide subunit comprised of alternating alpha- and is an element of-amino acids. The design features a novel 1,4-disubstituted-1,2,3-triazole 6-amino acid and its utility as a peptide backbone substitute. The N-Fmoc-protected is an element of-amino acid was synthesized in high yield and optical purity in three steps from readily available starting materials and was employed in solid-phase peptide synthesis to afford the desired cyclic peptide structure. The cyclic peptide self-assembly has been studied in solution by H-1 NMR and mass spectrometry and the resulting tubular ensemble characterized in the solid state by X-ray crystallography.