histidyl-phenylalanine

• 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: histidyl-phenylalanine
• 英文别名: 2-[[2-azaniumyl-3-(1H-imidazol-5-yl)propanoyl]amino]-3-phenylpropanoate
• 化学式: C₁₅H₁₈N₄O₃
• 分子量: 302.333
• InChiKey: XMAUFHMAAVTODF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  histidyl-phenylalanine 、 [ReOCl3(OPPh3)(SMe2)] 、 苯 以 乙腈 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  Binding of the Oxo−Rhenium(V) Core to Methionine and to N-Terminal Histidine Dipeptides

  摘要：

  The ReOX2(met) compounds (X = Cl, Br) adopt a distorted octahedral structure in which a carboxylato oxygen lies trans to the Re=O bond, whereas the equatorial plane is occupied by two cis halides, an NH2, and an SCH3 group. Coordination of the SCH3 unit creates an asymmetric center, leading to two diastereoisomers. X-ray diffraction studies reveal that the crystals of ReOBr2(D,L-met)(.)1/2H(2)O and ReOBr2(D,L-met)(.)1/2CH(3)OH contain only the syn isomer (S-CH3 bond on the side of the Re=O bond), whereas ReOCl2(D-met) and ReOCl2(D,L-met) consist of the pure anti isomer. H-1 NMR spectroscopy shows that both isomers coexist in equilibrium in acetone (anti/syn ratio = 1:1 for X = Br, 3:1 for X = Cl). Exchange between these two isomers is fast above room temperature, but it slows down below 0degreesC, and the sharp second-order spectra of both isomers at -20degreesC were fully assigned. The coupling constants are consistent with the solid-state conformations being retained in solution. Complexes of the type [ReOX2(His-aa)]X (X = Cl, Br) are isolated with the dipeptides His-aa (aa = Gly, Ala, Leu, and Phe). X-ray diffraction work on [ReOBr2(His-Ala)]Br reveals the presence of distorted octahedral cations containing the Re= O3+ core and a dipeptide coordinated through the histidine residue via the imidazole nitrogen, the terminal amino group, and the amide oxygen, the site trans to the Re=O bond being occupied by the oxygen. The alanine residue is ended by a protonated carboxylic group that does not participate in the coordination. The constant pattern of the H-1 NMR signals for the protons in the histidine residue confirms that the various dipeptides adopt a similar binding mode, consistent with the solid-state structure being retained in CD3OD solution.

  DOI：

  10.1021/ic048776e

文献信息

• FLUORESCENT NANOPARTICLES
  申请人：Laarmann Sven

  公开号：US20090226371A1

  公开（公告）日：2009-09-10

  The use of fluorescent nanoparticles comprising an inorganic core, a passivating layer and specific ligands having a hydrodynamic diameter of the inorganic core with the passivating layer of not more than 15 nm, preferably of not more than 10 nm, particularly preferably of not more than 5 nm, for preparing an in vivo diagnostic aid, the nanoparticles showing an emission of less than 700 nm.

  使用具有无机核、钝化层和特定配体的荧光纳米颗粒，其无机核的水动力直径与钝化层不超过15纳米，优选不超过10纳米，特别优选不超过5纳米，用于制备体内诊断辅助剂，该纳米颗粒显示出小于700纳米的发射。
• process for the preparation of optically-active cyanomethyl esters
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0109681A2

  公开（公告）日：1984-05-30

  Stereoisomerically-enriched cyanomethyl esters are prepared by treating a non-symmetrical ketene or an alpha-chiral carboxylic acid halide or reactive derivative thereof with an optically-active alphahydroxynitrile. Certain optically-active optionally substituted S-alphacyano-3-phenoxybenzyl alcohol intermediates are prepared by treating the corresponding aldehyde of ketone with a source of hydrogen cyanide in the presence of a substantially water-immiscible, aprotic solvent and a cyclo(D-phenylalanyl-D-histidine) as a catalyst.

  通过将非对称酮或α-手性羧酸卤化物或其活性衍生物与具有光学活性的α-羟腈进行处理，可制备立体异构体富集的氰甲基酯。某些具有光学活性的任选取代的 S-alphacyano-3-苯氧基苄醇中间体的制备方法是：在基本上不溶于水的壬烷溶剂和作为催化剂的环(D-苯丙氨酰-D-组氨酸)存在下，用氰化氢源处理相应的酮醛。
• Preparation of optically-active alpha-substituted carboxylic esters and acids
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0116914A1

  公开（公告）日：1984-08-29

  Optically-active alpha-substituted carboxylic esters are prepared by treating a non-symmetrical ketene with an alcohol in the presence of an optically-active amine catalyst. Hydrolysis of the resulting esters, yields the optically-active acid corresponding to the non-symmetrical ketene.

  光学活性α-取代羧酸酯是通过在光学活性胺催化剂存在下用醇处理非对称酮来制备的。水解生成的酯会产生与非对 称酮相对应的光学活性酸。
• Process for the preparation of optically-active cyanomethyl esters
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0291626A2

  公开（公告）日：1988-11-23

  Stereoisomerically-enriched cyanomethyl esters are prepared by treating a non-symmetrical ketene or an alpha-chiral carboxylic acid halide or reactive derivative thereof with an optically-active alpha-hydroxynitrile. Certain optically-active optionally substituted S-alpha-cyano-3-phenoxybenzyl alcohol intermediates are prepared by treating the corresponding aldehyde or ketone with a source of hydrogen cyanide in the presence of a substantially water-immiscible, aprotic solvent and a cyclo(D-phenylalanyl-D-histidine) as a catalyst.

  立体异构体富集氰基甲酯的制备方法是用光学活性的 α-羟腈处理非对称酮或α-手性羧酸卤化物或其活性衍生物。某些具有光学活性的任选取代的 S-α-氰基-3-苯氧基苄醇中间体的制备方法是：在基本上不溶于水的壬烷溶剂和作为催化剂的环(D-苯丙氨酰-D-组氨酸)存在下，用氰化氢源处理相应的醛或酮。
• Fluoreszenz-Nanopartikel
  申请人：Signalomics GmbH

  公开号：EP1787659A1

  公开（公告）日：2007-05-23

  Verwendung fluoreszierender Nanopartikel enthaltend einen anorganischen Kern, eine Passivierungsschicht und spezifische Liganden mit einem hydrodynamischen Durchmesser des anorganischen Kerns mit der Passivierungsschicht von nicht mehr als 15 nm, vorzugsweise von nicht mehr als 10 nm, besonders bevorzugt von nicht mehr als 5 nm zur Herstellung eines in vivo Diagnostikums, wobei die Nanopartikel eine Emission von weniger als 700 nm aufweisen.

  使用含有无机核心、钝化层和特定配体的荧光纳米粒子生产体内诊断剂，无机核心与钝化层的水动力直径不超过 15 纳米，最好不超过 10 纳米，尤其最好不超过 5 纳米，其中纳米粒子的发射波长小于 700 纳米。