L-mandelic acid-L-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: L-mandelic acid-L-phenylalanine
• 英文别名: N-((S)-mandeloyl)-L-phenylalanine；(2S)-2-[[(2S)-2-hydroxy-2-phenylacetyl]amino]-3-phenylpropanoic acid
• CAS: 127984-21-8
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: NGIIPASORMICME-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2-oxo-2-phenylacetamido)-3-phenylpropanoic acid 在 Cy-POP-Ae (Rh+) 氢气 作用下， 以 甲醇 为溶剂， 以47%的产率得到L-mandelic acid-L-phenylalanine
  参考文献：
  名称：

  α-酮酸衍生物与 Rh(I)-手性二亚膦酸盐体系的不对称氢化。卤化物反离子对不对称感应的影响

  摘要：

  具有二环己基膦氧基和二甲氨基部分的手性二次膦酸配体 (Cy-POP-AE) 可在温和条件下通过 Rh(I) 催化剂有效地对 N-(苯甲酰基甲酰基) 氨基酸进行不对称氢化。中性铑 (I) 前体在甲醇中实现双重不对称诱导，而阳离子前体导致主要由底物手性控制的不对称诱导。

  DOI：

  10.1246/bcsj.63.281

文献信息

• Alcaligenes faecalis penicillin G acylase-catalyzed enantioselective acylation of dl-phenylalanine and derivatives in aqueous medium
  作者：Xiangyu Gong、Erzheng Su、Pixiang Wang、Dongzhi Wei

  DOI：10.1016/j.tetlet.2011.08.056

  日期：2011.10

  A new strategy based on enantioselective acylation properties of relatively unknown penicillin G acylase from Alcaligenes faecalis has been developed for the production of pharmacologically interesting enantiomerically pure d-phenylalanine. In order to get high reaction rate and enantioselectivity, two key factors (pH and temperature) and eight different acyl donors were optimized, and the optimal

  已经开发了基于相对未知的粪便产青霉素的青霉素G酰基转移酶的对映选择性酰化性质的新策略，用于生产药理学上有趣的对映体纯的d-苯丙氨酸。为了获得高反应速率和对映选择性，对两个关键因素（pH和温度）和八个不同的酰基供体进行了优化，并使用苯乙酰胺作为酰基供体，在pH 10、35°C下进行了最佳的酰化反应。该对映选择性酰化方法还通过在对映纯中有效产生五种不同的对位取代的苯丙氨酸衍生物来说明。
• 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.
• Asymmetric Hydrogenation of α-Keto Acid Derivatives with Rh(I)–Chiral Diphosphinite System. Effect of Halide Counterion on the Asymmetric Induction
  作者：Takamichi Yamagishi、Satoru Ikeda、Tatsuya Egawa、Motowo Yamaguchi、Mitsuhiko Hida

  DOI：10.1246/bcsj.63.281

  日期：1990.1

  dicyclohexylphosphinooxy and dimethylamino moieties (Cy-POP-AE) was effective for the asymmetric hydrogenation of N-(benzoylformyl) amino acids by a Rh(I) catalyst under mild conditions. A neutral rhodium(I) precursor enabled a double asymmetric induction in methanol, while a cationic precursor caused an asymmetric induction controlled mainly by the substrate chirality.

  具有二环己基膦氧基和二甲氨基部分的手性二次膦酸配体 (Cy-POP-AE) 可在温和条件下通过 Rh(I) 催化剂有效地对 N-(苯甲酰基甲酰基) 氨基酸进行不对称氢化。中性铑 (I) 前体在甲醇中实现双重不对称诱导，而阳离子前体导致主要由底物手性控制的不对称诱导。