N-(tert-butoxycarbonyl)-L-tyrosyl-α-aminoisobutyric acid methyl ester | 69872-64-6

• 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-(tert-butoxycarbonyl)-L-tyrosyl-α-aminoisobutyric acid methyl ester
• 英文别名: Boc-Tyr-Aib-OMe；N-tert-butoxycarbonyl-L-tyrosyl-2-aminoisobutyric acid methyl ester；Boc-L-Tyr-Aib-OMe；methyl 2-[[(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-2-methylpropanoate
• CAS: 69872-64-6
• 化学式: C₁₉H₂₈N₂O₆
• 分子量: 380.441
• InChiKey: QNGPTNPKSIFIMM-AWEZNQCLSA-N

物化性质

• 熔点：
  122-128 °C
• 沸点：
  578.7±50.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  113.96
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-L-tyrosyl-α-aminoisobutyric acid methyl ester 在 sodium hydroxide 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 28.0h， 生成 (R,S)-N-(tert-butyloxycarbonyl)-L-tyrosyl-α-aminoisobutyrylglicine 1,3-dimethylbutylamide
  参考文献：
  名称：

  Investigation of the structural parameters involved in the .mu. and .delta. opioid receptor discrimination of linear enkephalin-related peptides

  摘要：

  The previous rules proposed for selective recognition of mu and delta opioid receptors by modified enkephalins were investigated through an extensive structure-activity study. Thus, modifications of the sequence of TRIMU 4 (Tyr-D-Ala-Gly-NHCH(CH3)CH2CH(CH3)2, a peptide that exhibits mu selectivity close to that of DAGO (Try-D-Ala-Gly-N(Me)Phe-Gly.ol), were performed for two positions, 2 and 4, critical for mu recognition. The drastic loss of potency following introduction of L-Ala or Aib in position 2 emphasizes the importance of the stereochemistry and the steric size of the X2 amino acid for optimal mu binding. The enhancement of the intrinsic flexibility of the C-terminal alkyl chain of TRIMU 4 through removal of a methyl group leads to TRIMU 5 (Tyr-D-Ala-Gly-NHCH2CH2CH(CH3)2), a peptide with a mu selectivity similar to that of DAGO. In contrast, introduction of an O-tert-butyl Ser2 residue increases affinity for delta receptors. In the hexapeptide series derived from DSLET (Tyr-D-Ser-Gly-Phe-Leu-Thr), a D-Thr2 moiety was shown to be very efficient in improving delta recognition and delta selectivity appeared also to be modulated by the nature of the sixth residue. The potencies of the 24 peptides studied to inhibit the electrically evoked contractions of the GPI or MVD are relatively well correlated with their affinities for brain mu or delta receptors labeled with [3H]DAGO or [3H]DSLET, respectively. Moreover, the analgesic potency (hot plate test) of the peptides is related to their affinity for rat brain mu receptors. The wide range of receptor affinities exhibited by the compounds reported here could be useful to study the physiological role of mu and delta receptors.

  DOI：

  10.1021/jm00397a019
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 N-(tert-butoxycarbonyl)-L-tyrosyl-α-aminoisobutyric acid methyl ester
  参考文献：
  名称：

  A new peptide motif in the formation of supramolecular double helices

  摘要：

  新型三肽结构单元Boc-Tyr-Aib-Xaa-OMe（Xaa = Leu/Ile/Ala）的单晶X射线衍射研究表明，这些肽采取β转角构象，在固态中通过多种非共价相互作用自组装形成超分子双螺旋结构，并且这些肽展现出III型N2吸附等温线。

  DOI：

  10.1039/c0cc04244g

文献信息

• Practical Peptide Synthesis Mediated by a Recyclable Hypervalent Iodine Reagent and Tris(4-methoxyphenyl)phosphine
  作者：Chi Zhang、Shan-Shan Liu、Bo Sun、Jun Tian

  DOI：10.1021/acs.orglett.5b02045

  日期：2015.8.21

  1,4-dione (p-BTFP-iodosodilactone, 1a) was synthesized and demonstrated to be an efficient hypervalent iodine(III) reagent for the synthesis of dipeptides from various standard amino acids, including sterically hindered amino acids, in good to high yields within 30 min in the presence of tris(4-methoxyphenyl)phosphine. In addition, the combined system of 1a/(4-MeOC6H4)3P was used to synthesize the

  6-（3,5-二（三氟甲基）苯基）-1 ħ，4 ħ -2aλ 3 -ioda -2,3- dioxacyclopenta [喜]茚-1,4-二酮（p -BTFP-iodosodilactone，1A）中的溶液在三（4-甲氧基苯基）膦的存在下，在30分钟内以高至高收率合成并证明是一种有效的高价碘（III）试剂，用于从各种标准氨基酸（包括位阻氨基酸）合成二肽。另外，使用1a /（4-MeOC 6 H 4）3 P的组合系统以保护形式合成五肽亮氨酸-脑啡肽。值得注意的是1a 反应后可以很容易地再生。
• Insights into self-assembling nanoporous peptide and in situ reducing agent
  作者：Poulami Jana、Sibaprasad Maity、Debasish Haldar

  DOI：10.1039/c0ce00143k

  日期：——

  A tripeptide containing an Aib (α-amino isobutyric acid) residue self-assembles to form porous nanomaterials in solid state. In spite of having a hollow nanotubular structure, the self-assembly nature of the peptide is different, which leads to the formation of pores with different internal diameters. The single-crystal X-ray diffraction study reveals that the peptide forms continuous hydrogen-bonded poly-disperse nanopores (3, 5 and 8 membered) starting from the β-turn conformation as an associating sub-unit. The field emission scanning electron micrograph (FESEM) shows that the average pore sizes are in the range of 20 to 200 nm, although a few large pores are also visible. Moreover, the peptide 1 acts as an in situ reducing agent to synthesize hexagonal gold nanoparticles (GNP).

  一种含有Aib(α-氨基异丁酸)残基的三肽在固态下自组装形成多孔纳米材料。尽管具有中空纳米管结构，但肽的自组装性质不同，导致形成具有不同内径的孔隙。单晶X射线衍射研究表明，肽从β-转角构象作为关联子单元开始，形成连续的氢键分散的纳米孔(3、5和8元)。场发射扫描电子显微镜(FESEM)显示，尽管也可见到一些较大的孔隙，但平均孔径在20到200纳米之间。此外，肽1作为原位还原剂用于合成六角形金纳米粒子(GNP)。
• A Mechanistic and Kinetic Study of the Formation of Metal Nanoparticles by Using Synthetic Tyrosine-Based Oligopeptides
  作者：Satyabrata Si、Rama Ranjan Bhattacharjee、Arindam Banerjee、Tarun K. Mandal

  DOI：10.1002/chem.200500834

  日期：2006.1.23

  of tyrosine residues in the peptide increases. The kinetic study, based on spectrophotometric measurements of the surface plasmon resonance optical property, shows that the rate of formation of gold nanoparticles was much faster at higher pH than at lower pH and was also dependent on the number of tyrosine residues present in the peptide. The dityrosine form of the peptide was found to retain reducing

  含有氧化还原活性酪氨酸残基的合成寡肽已用于制备金和银纳米粒子。在该还原过程中，来自肽的酪氨酸离子的电子通过形成酪氨酸基团在碱性pH下转移至金属离子，该酪氨酸基团最终在反应过程中转化为二氢酪氨酸形式。该反应机理已通过紫外可见光谱，荧光光谱和EPR光谱学得到证实，并发现是pH依赖性的。透射电子显微镜测量表明，金纳米颗粒的平均大小和单分散性随肽中酪氨酸残基数量的增加而增加。基于分光光度法测量表面等离振子共振光学特性的动力学研究，结果表明，金纳米颗粒的形成速率在较高的pH值下要比在较低的pH值下快得多，并且还取决于肽中存在的酪氨酸残基的数量。发现该肽的二酪氨酸形式保留了在碱性培养基中类似酪氨酸的还原特性。
• GACEL, G.;ZAJAC, J. M.;DELAY-GOYET, P.;DAUGE, V.;ROQUES, B. P., J. MED. CHEM., 31,(1988) N 2, 374-383
  作者：GACEL, G.、ZAJAC, J. M.、DELAY-GOYET, P.、DAUGE, V.、ROQUES, B. P.

  DOI：——

  日期：——