(S)-2-((R)-2-Benzoylamino-3-phenyl-propionylamino)-4-methylsulfanyl-butyric acid

• 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: (S)-2-((R)-2-Benzoylamino-3-phenyl-propionylamino)-4-methylsulfanyl-butyric acid
• 英文别名: (2S)-2-[[(2R)-2-benzamido-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid
• 化学式: C₂₁H₂₄N₂O₄S
• 分子量: 400.499
• InChiKey: FCZDJBFXGSPBAZ-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(METHYLSULFANYL)-2-[(2Z)-3-PHENYL-2-(PHENYLFORMAMIDO)PROP-2-ENAMIDO]BUTANOIC ACID 在 palladium on activated charcoal 氢气 、 palladium dichloride 作用下， 以 乙醇 为溶剂， 生成 (S)-2-((R)-2-Benzoylamino-3-phenyl-propionylamino)-4-methylsulfanyl-butyric acid 、 Bz-Phe-Met-OH
  参考文献：
  名称：

  Hydrogenation of complexes of diastereotopicN-benzoyldehydrodipeptides

  摘要：

  The replacement of the N-acetyl group by an N-benzoyl group in N-acyldehydrodipeptides results, first, in an increase in the asymmetric induction in their hydrogenation in the case of N-Bz-Delta Phe-(S)-Glu. N-Bz-(S)-Phe-(S)-Glu is obtained with a diastereomeric excess (de) of 52 %. Second, no poisoning of the Pd-catalyst by sulfur in N-Bz-Delta Phe-(S)-Met occurs, and N-Bz-(R)-Phe-(S)-Met is obtained with a de of 26 %. The formation of complexes of N-Bz-Delta Phe-AA with Ca2+ and Mg2+ ions does not, as a rule, affect the diastereoselectivity of the hydrogenation. The structure of the dehydrodipeptides has been determined on the basis of H-1 NMR spectra, potentiometric titration, and molecular mechanics calculations.

  DOI：

  10.1007/bf00717348