N-D-mandeloyl-D-phenylalanine | 127984-21-8

• 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: N-D-mandeloyl-D-phenylalanine
• 英文别名: N-((S)-mandeloyl)-L-phenylalanine；D-mandelic acid-L-phenylalanine；N-D-mandeloyl-L-phenylalanine；N-D-Mandeloyl-L-phenylalanin
• CAS: 127984-21-8；127984-22-9
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: NGIIPASORMICME-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  86.63
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-D-mandeloyl-D-phenylalanine 在 盐酸 作用下， 生成 L-苯丙氨酸
  参考文献：
  名称：

  Berlingozzi et al., Gazzetta Chimica Italiana, 1954, vol. 84, p. 383,391

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-2-乙酰氧基-2-苯乙酸 在 sodium hydroxide 、 氯化亚砜 作用下， 生成 N-D-mandeloyl-D-phenylalanine
  参考文献：
  名称：

  Berlingozzi et al., Gazzetta Chimica Italiana, 1954, vol. 84, p. 383,391

  摘要：

  DOI：

文献信息

• Investigating Chiral Recognizability of Diastereomeric Crystallization of Mandelic Acid and L-Phenylalanine
  作者：Jong Min Kim、Sang Mok Chang、In Ho Kim、Xuan-Hung Pham、Woo-Sik Kim

  DOI：10.1166/jnn.2012.6490

  日期：2012.9.1

  force measured with AFM exhibited a stronger molecular interaction between L-mandelic acid and 4-amino-L-phenylalanine than between D-mandelic acid and 4-amino-L-phenylalanine. Plus, the AFM results implied that the hydroxyl group abundance on the mandelic acid surface was a possible explanation for the different chiral selectivity of the L-phenylalanine.

  本研究研究了拆分剂（L-苯丙氨酸）对手性异构体（D / L-扁桃酸）的手性识别机理。根据NMR分析，即使两种非对映体溶液的化学位移没有差异，也观察到两种非对映体晶体之间的独特化学位移（L-扁桃酸-L-苯丙氨酸和D-扁桃酸-L-苯丙氨酸）。 。该结果表明拆分剂的手性识别主要发生在溶液中非对映异构体的结晶过程中。然后，通过热分析和原子力显微镜确认了非对映异构体的手性识别。L-扁桃酸-L-苯丙氨酸的非对映体晶体比D-扁桃酸-L-苯丙氨酸的非对映体晶体具有更高的晶格能量，因此热稳定性更高。而且，用AFM测量的粘合力表现出L-扁桃酸与4-氨基-L-苯丙氨酸之间的分子相互作用比D-扁桃酸与4-氨基-L-苯丙氨酸之间的分子相互作用更强。另外，原子力显微镜的结果暗示，扁桃酸表面的羟基丰度是L-苯丙氨酸的不同手性选择性的可能解释。
• Stereochemical effects in mass spectrometry. 7. Determination of absolute configuration of some organic molecules by reaction mass spectrometry
  作者：Yao-Zu Chen、Hung Li、Hou-Jun Yang、Su-Ming Hua、Hai-Quan Li、Fan-Zhi Zhao、Nen-Yu Chen

  DOI：10.1002/oms.1210231205

  日期：1988.12

  AbstractIt was found that in the chemical ionization (isobutane) mass spectra of some asymmetric secondary alcohols and α‐amino acids, when a pair of enantiomers (such as R‐ and S‐2‐phenyIbutyric anhydride, R‐ and S‐mandelic acid, R‐ and S‐2‐methylbutanoic acid or R‐ and S‐α‐phenyl ethyl amine) were used as reaction reagents, the relative abundances of characteristic ions formed by the stereoselective reaction between sample and reagent of the same configuration were much higher than those ions formed by the sample and a reagent of a different configuration. The absolute configuration of the sample molecule may be predicted by examination of mass spectra of the sample measured with R‐ and S‐reagent respectively. This approach proved to be a convenient way for determination of the absolute configurations of organic molecules on a micromole level by mass Spectrometry.