ethyl trifluoroacetyl-dimethylglycyl-(S)-2-α-ethylleucyl-dimethylglycyl-dimethylglycinate | 500905-38-4

• 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: ethyl trifluoroacetyl-dimethylglycyl-(S)-2-α-ethylleucyl-dimethylglycyl-dimethylglycinate
• CAS: 500905-38-4
• 化学式: C₂₄H₄₁F₃N₄O₆
• 分子量: 538.608
• InChiKey: YEWWWSOHKVRDEK-QHCPKHFHSA-N

物化性质

• 熔点：
  185-186 °C
• 沸点：
  694.7±55.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  37.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  142.7
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl trifluoroacetyl-dimethylglycyl-(S)-2-α-ethylleucyl-dimethylglycyl-dimethylglycinate 在 sodium tetrahydroborate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 68.0h， 生成 ethyl trifluoroacetyl-dimethylglycyl-dimethylglycyl-(S)-α-ethylleucyl-dimethylglycyl-dimethylglycinate
  参考文献：
  名称：

  Conformation of Peptides Containing a Chiral -Ethylated ,-Disubstituted -Amino Acid: (S)--Ethylleucine (=(2S)-2-Amino-2-ethyl-4-methylpentanoic Acid) within Sequences of Dimethylglycine and Diethylglycine Residues

  摘要：

  An optically active (S)-alpha-ethylleucine ((S)-alphaEtLeu) as a chiral alpha-ethylated alpha,alpha-disubstituted alpha-amino acid was synthesized by means of a chiral acetal auxiliary of (R,R)-cyclohexane-1,2-diol. The chiral alpha-ethylated alpha,alpha-disubstituted amino acid (S)-alphaEtLeu was introduced into the peptides constructed from 2aminoisobutyric acid (= dimethylglycine, Aib), and also into the peptide prepared from diethylglycine (Deg). The X-ray crystallographic analysis revealed that both right-handed (P) and left-handed (M) 3(10)-helical structures exist in the solid state of CF3CO-(Aib)(2)-[(S)-alphaEtLeu]-(Aib)(2)-OEt (14) and CF3CO-[(S)-alphaEtLeu]-(Deg)(4)-OEt (18), respectively. The IR, CD, and H-1-NMR spectra indicated that the dominant conformation of pentapeptides 14 and CF3CO-[(S)-alphaEtLeu]-(Aib)(4)-OEt (16) in solution is a 3(10)-helical structure, and that of 18 in solution is a planar C-5 conformation. The conformation of peptides was also studied by molecular-mechanics calculations.

  DOI：

  10.1002/1522-2675(200210)85:10<3197::aid-hlca3197>3.0.co;2-y
• 作为产物：
  描述：

  ethyl (S)-N-acetyl-α-ethylleucinate 在 盐酸 、 sodium tetrahydroborate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 200.0h， 生成 ethyl trifluoroacetyl-dimethylglycyl-(S)-2-α-ethylleucyl-dimethylglycyl-dimethylglycinate
  参考文献：
  名称：

  Conformation of Peptides Containing a Chiral -Ethylated ,-Disubstituted -Amino Acid: (S)--Ethylleucine (=(2S)-2-Amino-2-ethyl-4-methylpentanoic Acid) within Sequences of Dimethylglycine and Diethylglycine Residues

  摘要：

  An optically active (S)-alpha-ethylleucine ((S)-alphaEtLeu) as a chiral alpha-ethylated alpha,alpha-disubstituted alpha-amino acid was synthesized by means of a chiral acetal auxiliary of (R,R)-cyclohexane-1,2-diol. The chiral alpha-ethylated alpha,alpha-disubstituted amino acid (S)-alphaEtLeu was introduced into the peptides constructed from 2aminoisobutyric acid (= dimethylglycine, Aib), and also into the peptide prepared from diethylglycine (Deg). The X-ray crystallographic analysis revealed that both right-handed (P) and left-handed (M) 3(10)-helical structures exist in the solid state of CF3CO-(Aib)(2)-[(S)-alphaEtLeu]-(Aib)(2)-OEt (14) and CF3CO-[(S)-alphaEtLeu]-(Deg)(4)-OEt (18), respectively. The IR, CD, and H-1-NMR spectra indicated that the dominant conformation of pentapeptides 14 and CF3CO-[(S)-alphaEtLeu]-(Aib)(4)-OEt (16) in solution is a 3(10)-helical structure, and that of 18 in solution is a planar C-5 conformation. The conformation of peptides was also studied by molecular-mechanics calculations.

  DOI：

  10.1002/1522-2675(200210)85:10<3197::aid-hlca3197>3.0.co;2-y