Z-[L-(αMe)Val]2-NHtBu | 409320-08-7

• 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: Z-[L-(αMe)Val]2-NHtBu
• CAS: 409320-08-7
• 化学式: C₂₄H₃₉N₃O₄
• 分子量: 433.591
• InChiKey: MAOAJIRMNIDTFU-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  96.53
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Z-[L-(αMe)Val]2-NHtBu 生成 H-[L-(αMe)Val]4-NHtBu
  参考文献：
  名称：

  Nitroxyl Peptides as Catalysts of Enantioselective Oxidations

  摘要：

  The achiral, nitroxyl-containing a-amino acid TOAC (TOAC 2,2,6,6-tetramethylpiperidine-1-oxyl-4-amino-4-carboxylic acid), in combination with the chiral alpha-amino acid C-alpha-methyl valine [(alphaMe)Val]. was used to prepare short peptides (from di- to hexa-) that induced the enantioselective oxidation of racemic I-phenylethanol to acetophenone. The best catalyst was an N-alpha-acylated dipeptide alkylamide with the -TOAC-(alphaMe)Val- sequence folded in a stable, intramolecularly hydrogen-bonded beta-turn conformation with large. lipophilic (hydrophobic) N- and C-terminal blocking groups. We rationalized our findings by proposing models for the diastereomeric intermediates between (R)-[and (S)]-1-phenylethanol and the catalyst Fmoc-TOAC-L(alphaMe)Val-NHiPr, based on the X-ray diffraction structure of the latter.

  DOI：

  10.1002/1521-3765(20020104)8:1<84::aid-chem84>3.0.co;2-n
• 作为产物：
  描述：

  Cbz-L-(α-Me)Val-NH-t-Bu 生成 Z-[L-(αMe)Val]2-NHtBu
  参考文献：
  名称：

  Nitroxyl Peptides as Catalysts of Enantioselective Oxidations

  摘要：

  The achiral, nitroxyl-containing a-amino acid TOAC (TOAC 2,2,6,6-tetramethylpiperidine-1-oxyl-4-amino-4-carboxylic acid), in combination with the chiral alpha-amino acid C-alpha-methyl valine [(alphaMe)Val]. was used to prepare short peptides (from di- to hexa-) that induced the enantioselective oxidation of racemic I-phenylethanol to acetophenone. The best catalyst was an N-alpha-acylated dipeptide alkylamide with the -TOAC-(alphaMe)Val- sequence folded in a stable, intramolecularly hydrogen-bonded beta-turn conformation with large. lipophilic (hydrophobic) N- and C-terminal blocking groups. We rationalized our findings by proposing models for the diastereomeric intermediates between (R)-[and (S)]-1-phenylethanol and the catalyst Fmoc-TOAC-L(alphaMe)Val-NHiPr, based on the X-ray diffraction structure of the latter.

  DOI：

  10.1002/1521-3765(20020104)8:1<84::aid-chem84>3.0.co;2-n

文献信息

• Controlling the sign and magnitude of screw-sense preference from the C-terminus of an achiral helical foldamer
  作者：Bryden A. F. Le Bailly、Jonathan Clayden

  DOI：10.1039/c4cc03261f

  日期：——

  The global screw-sense preference of an achiral helical oligomer is best controlled from its C-terminus by a single Ala monomer.

  一个无手性螺旋寡聚体的全球螺旋方向偏好最好通过其C-末端由单个丙氨酸单体控制。