(2R,3S)-(-)-2,3-dimethylphenylalanine | 143789-84-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2R,3S)-(-)-2,3-dimethylphenylalanine
• 英文别名: (2R,3S)-2,3-Dimethylphenylalanine；(2R,3S)-2-amino-2-methyl-3-phenylbutanoic acid
• CAS: 143789-84-8
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: JIJODEXUWUVDAU-GZMMTYOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-(-)-2,3-dimethylphenylalanine 在 4-二甲氨基吡啶 、 氯化亚砜 作用下， 以 氘代氯仿 为溶剂， 反应 4.0h， 生成 methyl (2R,3S)-2-methyl-3-phenyl-2-[[(1S)-1-phenylethyl]carbamoylamino]butanoate
  参考文献：
  名称：

  New Amino Acids for the Topographical Control of Peptide Conformation: Synthesis of All the Isomers of .alpha.,.beta.-Dimethylphenylalanine and .alpha.,.beta.-Dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid of High Optical Purity

  摘要：

  The synthesis of all four diastereoisomers of alpha,beta-dimethylphenylalanine (4) as well as those of alpha,beta-dimethyl-1 ,2,3,4,-tetrahydroisoquinoline-3-carboxylic acid (5 and 6) have been accomplished in high yield and high optical purity. Molecular mechanics calculations on the N-alpha-acetyl and N- methylcarboxamide derivatives of (3R,4R)-6 and (3R,4S)-5 indicate large and moderate energy stabilization for the gauche(-) but not the gauche(+) side-chain conformers of (3R,4S)-5 and (3R,4R)-6, respectively. By symmetry rules, the same holds for (3S,4R)-5 and (3S,4S)-6, respectively. Thus, these amino acids are potential building blocks for the topographical design of peptides (Kazmierski et al., J. Am. Chem. Sec. 1991, 113, 2275-2283) by providing acylated 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives in which a gauche(-) and not a gauche(+) side-chain conformation is energetically more stable for the L amino acid. Synthetic details and implications of these new amino acids for peptide and protein design are discussed.

  DOI：

  10.1021/jo00086a033
• 作为产物：
  描述：

  在 盐酸 作用下， 以52%的产率得到(2R,3S)-(-)-2,3-dimethylphenylalanine
  参考文献：
  名称：

  Asymmetric Synthesis of β-Substituted α-Amino Acids Using 2H-Azirine-2-carboxylate Esters. Synthesis of 3,3-Disubstituted Aziridine-2-carboxylate Esters

  摘要：

  DOI：

  10.1021/jo9702610

文献信息

• Asymmetric Synthesis of β-Substituted α-Amino Acids Using 2<i>H</i>-Azirine-2-carboxylate Esters. Synthesis of 3,3-Disubstituted Aziridine-2-carboxylate Esters
  作者：Franklin A. Davis、Chang-Hsing Liang、Hu Liu

  DOI：10.1021/jo9702610

  日期：1997.6.13
• New Amino Acids for the Topographical Control of Peptide Conformation: Synthesis of All the Isomers of .alpha.,.beta.-Dimethylphenylalanine and .alpha.,.beta.-Dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid of High Optical Purity
  作者：Wieslaw M. Kazmierski、Zofia Urbanczyk-Lipkowska、Victor J. Hruby

  DOI：10.1021/jo00086a033

  日期：1994.4

  The synthesis of all four diastereoisomers of alpha,beta-dimethylphenylalanine (4) as well as those of alpha,beta-dimethyl-1 ,2,3,4,-tetrahydroisoquinoline-3-carboxylic acid (5 and 6) have been accomplished in high yield and high optical purity. Molecular mechanics calculations on the N-alpha-acetyl and N- methylcarboxamide derivatives of (3R,4R)-6 and (3R,4S)-5 indicate large and moderate energy stabilization for the gauche(-) but not the gauche(+) side-chain conformers of (3R,4S)-5 and (3R,4R)-6, respectively. By symmetry rules, the same holds for (3S,4R)-5 and (3S,4S)-6, respectively. Thus, these amino acids are potential building blocks for the topographical design of peptides (Kazmierski et al., J. Am. Chem. Sec. 1991, 113, 2275-2283) by providing acylated 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives in which a gauche(-) and not a gauche(+) side-chain conformation is energetically more stable for the L amino acid. Synthetic details and implications of these new amino acids for peptide and protein design are discussed.