[(1R,2R,5R)-2-(tert-Butoxycarbonylamino-methyl)-5-hydroxymethyl-cyclopentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester | 476371-57-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [(1R,2R,5R)-2-(tert-Butoxycarbonylamino-methyl)-5-hydroxymethyl-cyclopentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: tert-butyl N-[[(1R,2R,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(hydroxymethyl)cyclopentyl]methyl]carbamate
• CAS: 476371-57-0
• 化学式: C₂₇H₃₄N₂O₅
• 分子量: 466.577
• InChiKey: XETQXAWAKMRAPE-NXMSCROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1R,2R,5R)-2-(tert-Butoxycarbonylamino-methyl)-5-hydroxymethyl-cyclopentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 在 四丁基溴化铵 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以0.65 g的产率得到3-(tert-butoxycarbonylaminomethyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)cyclopentanecarboxylic acid
  参考文献：
  名称：

  Stereoselective Synthesis of 3-Substituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into Short 12-Helical β-Peptides That Fold in Water

  摘要：

  A stereoselective synthetic route is reported for the introduction of side chains at the 3-position of trans-2-aminocyclopentanecarboxylic acid (ACPC). Ring opening of the aziridine 2-benzyloxymethyl-6-azabicyclo[3.1.0]hexane with selected nucleophiles occurs in a regioselective manner and provides ACPC precursors with functional groups at the 3-position, trans to the 2-amino group. Oligomers composed of the 3-substituted ACPC residues maintain the 12-helical conformation displayed by the nonsubstituted analogues, as shown by their similar circular dichroism signatures. The added diversity of the new residues provides good dispersion of NMR signals, allowing the assignment of nearly all the NOE signals of a selected hexamer in aqueous solution. The NOES between protons on nonadjacent residues are characteristic of the 12-helix. 3-Substituted ACPC residues allow one to arrange specific functional groups in a geometrically defined fashion, which should facilitate the design of beta-peptides for biological applications.

  DOI：

  10.1021/ja0258778
• 作为产物：
  描述：

  (2-benzyloxymethyl-5-cyanocyclopentyl)carbamic acid benzyl ester 在 硼烷四氢呋喃络合物 、 氨 、 sodium 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 41.5h， 生成 [(1R,2R,5R)-2-(tert-Butoxycarbonylamino-methyl)-5-hydroxymethyl-cyclopentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of 3-Substituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into Short 12-Helical β-Peptides That Fold in Water

  摘要：

  A stereoselective synthetic route is reported for the introduction of side chains at the 3-position of trans-2-aminocyclopentanecarboxylic acid (ACPC). Ring opening of the aziridine 2-benzyloxymethyl-6-azabicyclo[3.1.0]hexane with selected nucleophiles occurs in a regioselective manner and provides ACPC precursors with functional groups at the 3-position, trans to the 2-amino group. Oligomers composed of the 3-substituted ACPC residues maintain the 12-helical conformation displayed by the nonsubstituted analogues, as shown by their similar circular dichroism signatures. The added diversity of the new residues provides good dispersion of NMR signals, allowing the assignment of nearly all the NOE signals of a selected hexamer in aqueous solution. The NOES between protons on nonadjacent residues are characteristic of the 12-helix. 3-Substituted ACPC residues allow one to arrange specific functional groups in a geometrically defined fashion, which should facilitate the design of beta-peptides for biological applications.

  DOI：

  10.1021/ja0258778

文献信息

• Beta-amino acids
  申请人：Gellman H. Samuel

  公开号：US20070123709A1

  公开（公告）日：2007-05-31

  Disclosed are β-amino acid monomers containing cylcoalkyl, cycloalkenyl, and heterocylic substituents which encompass the α and β carbons of the peptide backbone and β-polypeptides made from such monomers. Method of generating combinatorial libraries of polypeptides containing the β-peptide residues and libraries formed thereby are disclosed.

  本发明涉及包含环烷基、环烯基和杂环取代基的β-氨基酸单体，其包括肽骨架的α和β碳，以及由这样的单体制成的β-多肽。还公开了生成含β-肽残基的多肽组合库的方法以及由此形成的库。
• Stereoselective Synthesis of 3-Substituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into Short 12-Helical β-Peptides That Fold in Water
  作者：Matthew G. Woll、John D. Fisk、Paul R. LePlae、Samuel H. Gellman

  DOI：10.1021/ja0258778

  日期：2002.10.1

  A stereoselective synthetic route is reported for the introduction of side chains at the 3-position of trans-2-aminocyclopentanecarboxylic acid (ACPC). Ring opening of the aziridine 2-benzyloxymethyl-6-azabicyclo[3.1.0]hexane with selected nucleophiles occurs in a regioselective manner and provides ACPC precursors with functional groups at the 3-position, trans to the 2-amino group. Oligomers composed of the 3-substituted ACPC residues maintain the 12-helical conformation displayed by the nonsubstituted analogues, as shown by their similar circular dichroism signatures. The added diversity of the new residues provides good dispersion of NMR signals, allowing the assignment of nearly all the NOE signals of a selected hexamer in aqueous solution. The NOES between protons on nonadjacent residues are characteristic of the 12-helix. 3-Substituted ACPC residues allow one to arrange specific functional groups in a geometrically defined fashion, which should facilitate the design of beta-peptides for biological applications.