Z-L-Ala-D-Ala-OMe | 28944-89-0

• 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: Z-L-Ala-D-Ala-OMe
• 英文别名: methyl (2R)-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 28944-89-0
• 化学式: C₁₅H₂₀N₂O₅
• 分子量: 308.334
• InChiKey: CUCAZZQPISJXOS-WDEREUQCSA-N

物化性质

• 沸点：
  497.7±35.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-L-Ala-D-Ala-OMe 在 palladium on activated charcoal 氢气 作用下， 生成 cyclo-(D-Ala-L-Ala)
  参考文献：
  名称：

  Naraoka, Hiroshi; Harada, Kaoru, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1557 - 1560

  摘要：

  DOI：
• 作为产物：
  描述：

  2-((S)-2-Benzyloxycarbonylamino-propionylamino)-propionic acid methyl ester 生成 甲基N-[(苄氧基)羰基]-L-丙氨酰-L-丙氨酸酯 、 Z-L-Ala-D-Ala-OMe
  参考文献：
  名称：

  Receptor binding mimetics: A novel molecularly imprinted polymer

  摘要：

  A novel molecularly imprinted polymer was prepared by copolymerization of trimethylolpropane trimethacrylate (1) and methacrylic acid (3) in the presence of a dipeptide acting as the template. The recognition capability of the synthetic receptor-like binding sites produced in the polymer network for the peptide was demonstrated by using the polymer as a chiral stationary phase in HPLC. The polymer was superior to previously reported molecularly imprinted polymers in that unusually high racemic resolution and load capacity were demonstrated.

  DOI：

  10.1016/0040-4039(95)00559-u

文献信息

• Enantioselection in peptide bond formation
  作者：Roger R. Hill、David Birch、Graham E. Jeffs、Michael North

  DOI：10.1039/b211914e

  日期：2003.3.13

  Selectivity in abiotic condensations of amino acids remains controversial and stereochemically little explored. We find that competitive activated couplings of N-acyl derivatives of glycine, alanine, valine, proline and phenylalanine with binary, ternary and quaternary mixtures of amides and esters of the same group of amino acids show little selectivity among the reactants, except with respect to configuration, where a consistent and significant preference for heterochiral outcomes, mostly >80%, is observed. One possible explanation of this selectivity predicts a predisposition to homochiral coupling under conditions that would require the two carboxyl functions to be co-facial in the activated complex.

  无机物促成的氨基酸缩聚反应中选择性仍然备受争议，而立体化学方面的研究甚少。我们发现，以酰胺和酯组成的双组分、三组分以及四组分混合物为底物，对甘氨酸、丙氨酸、缬氨酸、脯氨酸和苯丙氨酸的N-酰基衍生物进行竞争性活化偶联的反应中，产物在底物分子层面选择性较低，但对映异构选择性较高，选择性系数大多大于80%。此类反应中优先生成异手性产物的一种可能的解释是，在两个羧基必须共面的活化复合物中，同手性偶联具有倾向性。
• Amino-acids and peptides. Part XXVIII. Determination of racemization in peptide synthesis by nuclear magnetic resonance spectroscopy
  作者：Boris Weinstein、Arthur E. Pritchard

  DOI：10.1039/p19720001015

  日期：——

  Diastereoisomeric aromatic alanyl peptides possess different n.m.r. spectra owing to a diamagnetic shielding phenomenon. Observation of the shifted methyl resonance is an excellent procedure for the study of racemization in peptide synthesis. Eight alanyl dipeptides are available as models for the evaluation and testing of any N-acyl protecting group or coupling agent. The method is general, convenient

  由于抗磁屏蔽现象，非对映异构的芳族丙氨酰肽具有不同的nmr光谱。移位的甲基共振的观察是研究肽合成中外消旋作用的极好方法。八种丙氨酰二肽可用作评估和测试任何N-酰基保护基或偶联剂的模型。该方法通用，方便，快速，灵敏。
• Conformational effects in reversed-phase liquid chromatographic separation of diastereomers of cyclic dipeptides
  作者：Noriaki. Funasaki、Sakae. Hada、Saburo. Neya

  DOI：10.1021/ac00062a010

  日期：1993.7.15

  The capacity factors, k', of 11 cyclic dipeptides (X-Y) including diastereomers have been determined on an RP-HPLC column in 30% and 50% methanol and 10%, 30%, and 50% acetonitrile solutions. These factors are roughly correlated with hydrophobic parameters, such as octanol-water partition coefficients estimated and k' values for alcohols. For a pair of diastereomers of cyclic (L-X-L-Phe) and (L-X-D-Phe) derivatives k'LL is larger than k'LD, and for cyclic (D-Ala-L-Trp) and (L-Ala-L-Trp) k'LL is smaller than k'DL, particularly in highly aqueous solutions. These elution orders can be well predicted by the holistic molecular surface area approach which takes into account the folded structures of cyclic dipeptides. The present results will be useful for prediction of the log k' values of larger peptides and the hydrophobicity and related properties of peptides.
• KOGA, KENJI;SASAKI, SHIGEKI, PURE AND APPL. CHEM., 60,(1988) N 4, 539-543
  作者：KOGA, KENJI、SASAKI, SHIGEKI

  DOI：——

  日期：——