ethyl trifluoroacetyl-(S)-2-butyl-2-ethylglycyl-(S)-2-butyl-2-ethylglycyl-(S)-2-butyl-2-ethylglycinate | 316159-49-6

• 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-(S)-2-butyl-2-ethylglycyl-(S)-2-butyl-2-ethylglycyl-(S)-2-butyl-2-ethylglycinate
• 英文别名: CF3CO-[(S)-Beg]3-OEt；ethyl (2S)-2-ethyl-2-[[(2S)-2-ethyl-2-[[(2S)-2-ethyl-2-[(2,2,2-trifluoroacetyl)amino]hexanoyl]amino]hexanoyl]amino]hexanoate
• CAS: 316159-49-6
• 化学式: C₂₈H₅₀F₃N₃O₅
• 分子量: 565.717
• InChiKey: JWJWNPNNGYQIAW-QKDODKLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  39
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl trifluoroacetyl-(S)-2-butyl-2-ethylglycyl-(S)-2-butyl-2-ethylglycyl-(S)-2-butyl-2-ethylglycinate 在 sodium tetrahydroborate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 ethyl trifluoroacetyl-(S)-2-butyl-2-ethylglycyl-(S)-2-butyl-2-ethylglycyl-(S)-2-butyl-2-ethylglycinyl-(S)-2-butyl-2-ethylglycinyl-(S)-2-butyl-2-ethylglycinyl-(S)-2-butyl-2-ethylglycinate
  参考文献：
  名称：

  The First Fully Planar C ₅ ‐Conformation of Homooligopeptides Prepared from a Chiral α ‐Ethylated α , α ‐Disubstituted Amino Acid: ( S )‐Butylethylglycine (=(2 S )‐2‐Amino‐2‐ethylhexanoic Acid)

  摘要：

  An optically active alpha -ethylated alpha,alpha -disubstituted amino acid, (S)-butylethylglycine (= (2S)-2-amino-2-ethylhexanoic acid; (S)-Beg; (S)-2),was prepared starring from butyl ethyl ketone (1) by the Strecker method and enzymatic kinetic resolution of the racemic amino acid. Homooligopeptides containing (S)-Beg (up to hexapeptide) were synthesized by conventional solution methods. An ethyl cater was used for the protection at the C-terminus, and a trifluoroacetyl group was used for the N-terminus of the peptides. Thr structures of tri- and tetrapeptides 5 and 6 in the solid state were solved by X-ray crystallographic analysis, and were shown to have a bent planar C-conformation (tripeptide) and a fully planar C-5-conformation (tetrapeptide) (see Figs. I and 2, resp.). The IR and H-1-NMR spectra of hexapeptide 8 revealed that the dominant conformation in CDCl3, solution was also a fully planar C-5-conformation, These results show for the first time that the preferred conformation of homopeptides containing a chiral alpha -ethylated alpha,alpha -disubstituted amino acid is a planar C-5-conformation.

  DOI：

  10.1002/1522-2675(20001004)83:10<2823::aid-hlca2823>3.0.co;2-#
• 作为产物：
  描述：

  3-庚酮 在 盐酸 、 porcine liver esterase 、 sodium tetrahydroborate 、 硫酸 、 氯化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 phosphate buffer 、 乙醇 、 水 、 乙腈 为溶剂， 反应 173.5h， 生成 ethyl trifluoroacetyl-(S)-2-butyl-2-ethylglycyl-(S)-2-butyl-2-ethylglycyl-(S)-2-butyl-2-ethylglycinate
  参考文献：
  名称：

  The First Fully Planar C ₅ ‐Conformation of Homooligopeptides Prepared from a Chiral α ‐Ethylated α , α ‐Disubstituted Amino Acid: ( S )‐Butylethylglycine (=(2 S )‐2‐Amino‐2‐ethylhexanoic Acid)

  摘要：

  An optically active alpha -ethylated alpha,alpha -disubstituted amino acid, (S)-butylethylglycine (= (2S)-2-amino-2-ethylhexanoic acid; (S)-Beg; (S)-2),was prepared starring from butyl ethyl ketone (1) by the Strecker method and enzymatic kinetic resolution of the racemic amino acid. Homooligopeptides containing (S)-Beg (up to hexapeptide) were synthesized by conventional solution methods. An ethyl cater was used for the protection at the C-terminus, and a trifluoroacetyl group was used for the N-terminus of the peptides. Thr structures of tri- and tetrapeptides 5 and 6 in the solid state were solved by X-ray crystallographic analysis, and were shown to have a bent planar C-conformation (tripeptide) and a fully planar C-5-conformation (tetrapeptide) (see Figs. I and 2, resp.). The IR and H-1-NMR spectra of hexapeptide 8 revealed that the dominant conformation in CDCl3, solution was also a fully planar C-5-conformation, These results show for the first time that the preferred conformation of homopeptides containing a chiral alpha -ethylated alpha,alpha -disubstituted amino acid is a planar C-5-conformation.

  DOI：

  10.1002/1522-2675(20001004)83:10<2823::aid-hlca2823>3.0.co;2-#