N-(2,4-dinitrophenyl)-D-valine | 37696-35-8

• 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-(2,4-dinitrophenyl)-D-valine
• 英文别名: DNP-D-valine；N-(2,4-dinitro-phenyl)-D-valine；N-(2,4-Dinitro-phenyl)-D-valin；N-(2,4-Dinitro-phenyl)-D-valin；2,4-Dinitrophenyl-D-valin；(2R)-2-(2,4-dinitroanilino)-3-methylbutanoic acid
• CAS: 37696-35-8
• 化学式: C₁₁H₁₃N₃O₆
• 分子量: 283.241
• InChiKey: AYLCDVYHZOZQKM-SNVBAGLBSA-N

物化性质

• 沸点：
  504.1±50.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  D-缬氨酸 、 2,4-二硝基氟苯 生成 N-(2,4-dinitrophenyl)-D-valine
  参考文献：
  名称：

  氨基酸和多肽。第十部分。环二肽抗生素新家族成员莫纳霉素的表征

  摘要：

  莫纳霉素是一种结晶的抗菌制剂，从牙买加链霉菌的培养物中分离出来，由十五种环六肽肽的混合物组成，其中六种含氯。每个分子种类由一个α-羟基酸残基（L -2-羟基-3-甲基丁酸或L -2-羟基-3-甲基戊酸）和五个α-氨基或亚氨基酸残基组成。后者由N-甲基-D-亮氨酸，L-脯氨酸（或反式-4-甲基L-脯氨酸），D-异亮氨酸（或D-缬氨酸），（3 R）-哌嗪酸[或（3 R， 5 S）-5-氯哌嗪酸或（3R）-4,5（或5,6）-脱氢哌嗪酸]和（3 S，5 S）-5-羟基哌嗪酸。名称哌嗪酸被指定为六氢哒嗪-3-羧酸。

  DOI：

  10.1039/j39710000514

文献信息

• Direct Resolution of Optically Active Isomers on Chiral Packings Containing Ergoline Skeletons. 5. Enantioseparation of Amino Acid Derivatives
  作者：A. Messina、A. M. Girelli、M. Flieger、M. Sinibaldi、P. Sedmera、L. Cvak

  DOI：10.1021/ac950698c

  日期：1996.4.1

  alkaloid-based chiral stationary phase preparation is described. Synthesis is based on bonding the allyl derivative of terguride to mercaptopropylsilanized silica gel. The packing exhibits higher content of chiral selector, stability, reproducibility, and enantioselectivity toward amino acids compared to that previously studied. The chromatographic behavior of amino acids with different side chains and substituent

  描述了一种基于麦角生物碱的手性固定相制备的新方法。合成是基于将特固脲的烯丙基衍生物与巯基丙基硅烷化的硅胶结合。与先前研究的相比，该填料表现出更高的手性选择剂含量，稳定性，可再现性和对氨基酸的对映选择性。研究了具有不同侧链和取代基的氨基酸的色谱行为，以便更深入地了解对映鉴别机理，并确定特固利作为此类化合物的手性选择剂的局限性和强度。检查了多种因素，包括流动相参数，例如pH，离子强度，有机改性剂的含量和性质以及温度。
• AMIDOMYCIN, A NEW ANTIBIOTIC FROM A STREPTOMYCES SPECIES, CHEMICAL STRUCTURE
  作者：L. C. Vining、W. A. Taber

  DOI：10.1139/v57-151

  日期：1957.10.1

  Amidomycin, an antibiotic active primarily against yeast, has been isolated from a Streptomyces species. The Compound C₁₀H₆₈O₁₂N₄. is neutral, optically active, and shows no unsaturation nor characteristic light absorption maxima. It is composed of 4 moles each of D(−)-valine and D(−)-α-hydroxyisovaleric acid, linked alternately by ester and amide bonds to form a 24-membered ring (I). This structure is assigned from the following observations: on mild alkaline hydrolysis 4 moles of alkali are consumed with formation of a hydroxy acid, C₁₀H₁₉O₄N (II). The latter on distillation gave a crystalline lactone, C₁₀H₁₇O₃N, considered to be 3,6-diisopropyl-2,5-diketomorpholine (III), which was hydrolyzed to give 1 mole each of D(−)-valine and D(−)-α-hydroxyisovaleric acid.Amidomycin is closely related to valinomycin, an antibiotic isolated from Streptomycesfulvissimus and shown to be a 24-membered ring compound containing D(−)-valine, D(−)-α-hydroxyisovaleric acid, L(+)-valine, and L(−)-lactic acid. It also resembles the enniatins, produced by certain species of Fusarium, but differs from these compounds in the number of units in the ring structure as well as in containing D(−)-valine rather than an N-methyl-L-amino acid.

  Amidomycin是一种主要对酵母菌具有活性的抗生素，已从链霉菌属中分离出来。该化合物C₁₀H₆₈O₁₂N₄是中性的，具有光学活性，不含不饱和度，也没有特征性的光吸收峰值。它由4摩尔D(−)-缬氨酸和D(−)-α-羟基异丁酸交替连接形成一个24元环（I）。这种结构是根据以下观察而确定的：在温和的碱性水解中，4摩尔碱被消耗，并形成一个羟基酸C₁₀H₁₉O₄N（II）。后者经蒸馏得到一个结晶内酯，C₁₀H₁₇O₃N，被认为是3,6-二异丙基-2,5-二酮吗啉（III），它被水解为1摩尔D(−)-缬氨酸和D(−)-α-羟基异丁酸。Amidomycin与链霉菌fulvissimus分离的一种抗生素缬氨酸霉素密切相关，后者被证实是一种24元环化合物，含有D(−)-缬氨酸、D(−)-α-羟基异丁酸、L(+)-缬氨酸和L(−)-乳酸。它也类似于某些种类的镰刀菌产生的恩尼亚酮，但与这些化合物不同的是，它的环结构中的单元数量不同，并且含有D(−)-缬氨酸而不是N-甲基-L-氨基酸。
• Circular dichroism, ultraviolet, and proton nuclear magnetic resonance spectroscopic studies of the chiral recognition mechanism of .beta.-cyclodextrin
  作者：Song. Li、William C. Purdy

  DOI：10.1021/ac00037a019

  日期：1992.7.1

  The chiral recognition mechanism of beta-cyclodextrin was studied by UV-visible, circular dichroism, and proton nuclear magnetic resonance spectroscopic methods. The D and L enantiomers of DNP-valine, DNP-leucine, and DNP-methionine were used as model solutes. The results indicate that the dinitrophenyl group, which forms stable inclusion complexes with the beta-cyclodextrin cavity and places the other functional groups around the chiral center in association with the hydroxyl groups at the edge of the cavity, plays a very important role in the chiral recognition. The alkyl groups of amino acids, which form a secondary inclusion complex with another beta-cyclodextrin cavity (in the case of DNP-L-amino acids) or are sterically repulsed by the hydroxyl groups at the edge of the cavity (in the case of DNP-D-amino acids), are also major contributors to the chiral recognition process. The dissociation constants of the inclusion complexes of beta-cyclodextrin with these model compounds were also obtained from the changes of UV absorbance, elipticity, and chemical shifts, respectively. It was found that the DNP-L-amino acids always have smaller dissociation constants than the D-enantiomers.
• BARRA, M.;ROSSI, RITA H. DE, J. ORG. CHEM., 54,(1989) N1, C. 5020-5025
  作者：BARRA, M.、ROSSI, RITA H. DE

  DOI：——

  日期：——