Fmoc-TOAC-L-(αMe)Val-NHtBu | 409319-89-7

• 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: Fmoc-TOAC-L-(αMe)Val-NHtBu
• CAS: 409319-89-7
• 化学式: C₃₅H₄₉N₄O₅
• 分子量: 605.798
• InChiKey: DEPUZNMMYQAXFQ-UMSFTDKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Fmoc-TOAC-L-(αMe)Val-NHtBu 在 二乙胺 作用下， 生成 H-TOAC-L-(αMe)Val-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：

  (S)-(+)-2-benzyloxycarbonylamino-2,3-dimethylbutanoic acid 在 N-羟基-7-氮杂苯并三氮唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 生成 Fmoc-TOAC-L-(αMe)Val-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

• Nitroxyl Peptides as Catalysts of Enantioselective Oxidations
  作者：Fernando Formaggio、Marcella Bonchio、Marco Crisma、Cristina Peggion、Stefano Mezzato、Alessandra Polese、Alessandra Barazza、Sabrina Antonello、Flavio Maran、Quirinus B. Broxterman、Bernard Kaptein、Johan Kamphuis、Rosa Maria Vitale、Michele Saviano、Ettore Benedetti、Claudio Toniolo

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

  日期：2002.1.4

  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.