trifluoroacetyl-(S)-α-ethylleucine | 500905-36-2

• 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: trifluoroacetyl-(S)-α-ethylleucine
• 英文别名: 2-Ethyl-N-(trifluoroacetyl)-L-leucine；(2S)-2-ethyl-4-methyl-2-[(2,2,2-trifluoroacetyl)amino]pentanoic acid
• CAS: 500905-36-2
• 化学式: C₁₀H₁₆F₃NO₃
• 分子量: 255.237
• InChiKey: QJJLFUBLVHSNIM-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trifluoroacetyl-(S)-α-ethylleucine 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 104.0h， 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
• 作为产物：
  描述：

  ethyl (2R)-2-ethyl-3-[(1R,2R)-2-hydroxycyclohexyloxy]-2-(1-methylpropyl)but-3-enoate 在 盐酸 、 sodium azide 、 甲烷磺酸 、 三氟化硼乙醚 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 121.0h， 生成 trifluoroacetyl-(S)-α-ethylleucine
  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

文献信息

• An Extended Planar C5 Conformation and a 310-Helical Structure of Peptide Foldamer Composed of Diverse -Ethylated ,-Disubstituted -Amino Acids
  作者：Masakazu Tanaka、Shin Nishimura、Makoto Oba、Yosuke Demizu、Masaaki Kurihara、Hiroshi Suemune

  DOI：10.1002/chem.200204476

  日期：2003.7.7

  active peptide foldamers Tfa-[(S)-(alphaEt)Leu]-[(S)-(alphaEt)Nva]-Deg-[(S)-(alphaEt)Nle]-OEt (10) and Tfa-[(S)-(alphaEt)Val]-[(S)-(alphaEt)Leu]-[(S)-(alphaEt)Nva]-Deg-[(S)-(alphaEt)Nl e]-OEt (11) composed of diverse alpha-ethylated alpha,alpha-disubstituted alpha-amino acids were synthesized. The dominant conformation of these peptides in solution was an unusual, fully extended planar conformation, and

  光学活性肽折叠剂Tfa-[（S）-（alphaEt）Leu]-[（S-（alphaEt）Nva] -Deg-[（S）-（alphaEt）Nle] -OEt（10）和Tfa-[（ S）-（alphaEt）Val]-[（S）-（alphaEt）Leu]-[（S）-（alphaEt）Nva] -Deg-[（S）-（alphaEt）Nle e] -OEt（11）组成合成了多种α-乙基化的α，α-二取代的α-氨基酸。这些肽在溶液中的主要构象是一个不寻常的，完全延伸的平面构象，并且在晶体状态下是右旋（P）和左旋（M）3（10）螺旋结构，其中10和P图11中的3（10）-螺旋结构。由手性α-乙基化的α，α-二取代的α-氨基酸制备的肽的优选平面C（5）构象与由手性α-甲基化的α，制备的肽的3（10）-螺旋结构完全不同，
• 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
  作者：Makoto Oba、Masakazu Tanaka、Masaaki Kurihara、Hiroshi Suemune

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

  日期：2002.10

  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.