Boc-Tyr-Pro-OH

• 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: Boc-Tyr-Pro-OH
• 英文别名: t-Butyloxycarbonyl-tyrosyl-proline；(2S)-1-[(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]pyrrolidine-2-carboxylic acid
• 化学式: C₁₉H₂₆N₂O₆
• 分子量: 378.425
• InChiKey: NSIPXPQHZLNRJQ-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Tyr-Pro-OH 在 碳酸氢钠 、 三氟乙酸 作用下， 生成 环(脯氨酸一酪氨酸)
  参考文献：
  名称：

  Cyclodipeptides: Structure and conformation of cyclo(tyrosyl-prolyl)

  摘要：

  The structure and conformation of the cyclodipeptide, cyclo(Tyrosyl-Prolyl), cyclo(Tyr-Pro) have been investigated with X-ray crystallographic and spectroscopic methods. Two conformations of cyclo(Tyr-Pro) crystallized in the space group P2(1)2(1)2 with cell dimensions a = 11.890(3), b = 12.057(1), c = 18.528(4). Both these conformations are uncommon for cyclodipeptides containing a proline residue. The tyrosyl side chains of these conformers are folded towards the diketopiperazine (DKP) ring. The DKP ring adopts a flattened chair conformation in contrast to the typical boat conformation generally observed for DKP rings. The conformation of the pyrrolidine ring can be described as a pseudo C2 symmetrical twist. One intermolecular hydrogen bond was observed for each of the two conformations of cyclo(Tyr-Pro). The hydrogen of the hydroxyl group of the tyrosyl residue is hydrogen bonded to the oxygen of the carbonyl group of the diketopiperazine ring, i.e., the carbonyl group originating from the tyrosyl residue. NMR spectroscopic studies indicated a different conformation for cyclo(Tyr-Pro) in solution similar to the generally observed conformation of cyclodipeptides, i.e., extended aromatic side chain and boat conformation for the DKP ring.

  DOI：

  10.1007/bf01160980
• 作为产物：
  描述：

  Boc-Tyr-Pro-OMe 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以71%的产率得到Boc-Tyr-Pro-OH
  参考文献：
  名称：

  通过选择性呋喃氧化裂解短时间合成氧杂环丁烷和氮杂环丁烷3-芳基-3-羧酸衍生物。

  摘要：

  尽管四元环为药物化学提供了引人注目的理化性质，但它们仍然是未开发的基序。带有氧杂环丁烷，氮杂环丁烷和环丁烷的丙烯酸可以分两个步骤制备：从四元环醇底物进行的Friedel-Crafts催化反应，然后进行温和的氧化裂解。产品作为构建基块的适用性体现在其易于纯化和易于衍生化方面。实例包括杂芳族化合物和芳基三氟甲磺酸酯，以及氧杂环丁烷衍生的芬芬药物类似物和含有氮杂环丁烷氨基酸残基的新内啡肽衍生物。

  DOI：

  10.1021/acs.orglett.0c01214

文献信息

• Efficient chemo-enzymatic synthesis of endomorphin-1 using organic solvent stable proteases to green the synthesis of the peptide
  作者：Honglin Sun、Bingfang He、Jiaxing Xu、Bin Wu、Pingkai Ouyang

  DOI：10.1039/c1gc15042a

  日期：——

  (Tyr-Pro-Trp-Phe-NH2, EM-1), an effective analgesic, was efficiently synthesized by a combination of enzymatic and chemical methods. Peptide Boc-Trp-Phe-NH2 was synthesized with a high yield of 97.1% by the solvent-stable protease WQ9-2 in a 20% methanol medium. The maximum concentration (141 g L−1) of Boc-Trp-Phe-NH2 was obtained with an economical molar ratio of the substrate of 1:1. The products crystallized

  内啡肽1（Tyr-Pro-Trp-Phe-NH 2，EM-1），有效 止痛药通过酶促方法和化学方法的有效合成。 肽类Boc-Trp-Phe-NH 2的合成产率高达97.1％。溶剂在20％甲醇培养基中的稳定蛋白酶WQ9-2。在经济的底物摩尔比为1 ：1的情况下，获得Boc-Trp-Phe-NH 2的最大浓度（141 g L -1）。纯化，然后通过以下方式删除Boc小组： 三氟乙酸 产生 色氨酸-苯丙氨酸-NH 2。使用高效混合碳酸酐 方法， Boc-Tyr-Pro-OH是化学合成的。通过另一种有机化合物合成了四肽Boc-Tyr-Pro-Trp-Phe-NH 2，收率为84.5％。溶剂耐蛋白酶，PT121，来自 Boc-Tyr-Pro-OH和Trp-Phe-NH 2在有机-水双相系统中，并用乙酸乙酯，移动合成的平衡。EM-1是通过从Boc-Tyr-Pro-Trp-Phe-NH 2中除去Boc基
• Synthesis, Cytotoxic and Antimicrobial Screening of a Proline-Rich Cyclopolypeptide
  作者：Rajiv Dahiya、Akhilesh Kumar、Rajul Gupta

  DOI：10.1248/cpb.57.214

  日期：——

  Present study describes the first total synthesis of a cyclic heptapeptide, stylisin 1 (8) via coupling of tetrapeptide Boc-L-tyrosinyl-L-prolyl-L-leucyl-L-proline-OH and tripeptide L-phenylalanyl-L-isoleucyl-L-proline-OMe followed by cyclization of linear heptapeptide segment. Structure elucidation of synthesized cyclopeptide was done on basis of detailed spectral as well as elemental analysis. From the results of pharmacological screening, it was concluded that cyclopeptide 8 possessed moderate cytotoxicity against Dalton's lymphoma ascites (DLA) and Ehrlich's ascites carcinoma (EAC) cell lines with IC50 (inhibitory concentration, 50%) values of 10.6 and 14.6 μM. Furthermore, cyclopeptide 8 exhibited moderate to good antimicrobial activity against Gram −ve (negative) bacteria Klebsiella pneumoniae and Pseudomonas aeruginosa, dermatophytes and Candida albicans with minimum inhibitory concentration (MIC) of 6 μg/ml.

  本研究描述了首个环七肽stylisin 1（8）的全程合成，通过四肽Boc-L-酪氨酰-L-脯氨酰-L-亮氨酰-L-脯氨酸-OH与三肽L-苯丙氨酰-L-异亮氨酰-L-脯氨酸-OMe的耦合，随后进行线性七肽片段的环化。合成环肽的结构阐明基于详细的谱学及元素分析。从药理筛选结果得出，环肽8对Dalton淋巴瘤腹水（DLA）和Ehrlich腹水癌（EAC）细胞系表现出中等细胞毒性，IC50（抑制浓度，50%）值分别为10.6和14.6 μM。此外，环肽8对革兰氏阴性菌肺炎克雷伯菌和铜绿假单胞菌、皮肤真菌及白色念珠菌表现出中等至良好的抗微生物活性，最小抑制浓度（MIC）为6 μg/ml。
• Endomorphin-1 analogs containing α-methyl-β-amino acids exhibit potent analgesic activity after peripheral administration
  作者：Yuan Wang、Junxian Yang、Xin Liu、Long Zhao、Dongxu Yang、Jingjing Zhou、Dan Wang、Lingyun Mou、Rui Wang

  DOI：10.1039/c7ob01115f

  日期：——

  This study describes the design and synthesis of endomorphin-1 analogs containing C-terminal aromatic α-methyl-β-amino acids and an N-terminal native tyrosine or 2,6-dimethyl-tyrosine. We show that, in comparison with the parent peptide, these analogs exhibit improved bioactivity and blood–brain barrier penetration after intravenous administration, and have a lower tendency to induce constipation and

  这项研究描述了含有C末端芳香族α-甲基-β-氨基酸和N末端天然酪氨酸或2,6-二甲基酪氨酸的内啡肽-1类似物的设计和合成。我们显示，与母体肽相比，这些类似物在静脉内给药后表现出更高的生物活性和血脑屏障渗透性，并且比吗啡具有更低的诱发便秘和镇静作用的趋势。
• Exclusive Affinity-Labeling of<i>μ</i>Opioid Receptors by Morphiceptin Analogs Containing<i>S</i>-(3-Nitro-2-pyridylthio)cysteine
  作者：Shihoko Motoyama、Kiyoshi Takada、Teruo Yasunaga、Tsugumi Fujita、Yasuyuki Shimohigashi

  DOI：10.1246/bcsj.69.3607

  日期：1996.12

  The S-(3-nitro-2-pyridylthio) (Npys) group only reacts with a free mercapto group to form a disulfide bond. A series of morphiceptin analogs containing SNpys–cysteine were designed and synthesized for specific affinity-labeling of μ opioid receptors. Affinity-labeling of opioid receptors was monitored and evaluated by radioligand receptor binding assays using rat brain membranes and specific tritium-labeled ligands of enkephalin analogs. It was found that analogs with Cys(Npys) at position 4 or 5 bind covalently to μ receptors, but not to δ receptors, resulting in a discriminative and exclusive affinity labeling of μ opioid receptor subtype.

  S-(3-硝基-2-吡啶硫基)(NpyS)基团仅与游离巯基反应形成二硫键。设计并合成了一系列含有SNpys-半胱氨酸的吗啡酚类似物，用于对μ阿片受体进行特异性亲和标记。通过使用大鼠脑膜和特定氚标记的脑啡肽类似物配体进行放射配体受体结合试验，监测和评估了阿片受体的亲和标记。研究发现，第4或5位含有Cys(NpyS)的类似物能够共价结合μ受体，但不能结合δ受体，从而实现了对μ阿片受体亚型的区分性和专一性亲和标记。
• Studies on .ALPHA.2-plasmin inhibitor fragment T-11. I. Synthesis of the protected hexadecapeptide ester corresponding to positions 11 through 26 of .ALPHA.2-plasmin inhibitor fragment T-11.
  作者：TAKASHI SASAKI、SUMIRO ISODA

  DOI：10.1248/cpb.35.2797

  日期：——

  The protected hexadecapeptide ester corresponding to positions 11 through 26 of human α2-plasmin inhibitor fragment T-11, which consists of 26 amino acids and binds to the plasmin (ogen) lysine-binding site (s), was synthesized by assembling five peptide fragments by the azide method or the dicyclohexylcarbodiimide-N-hydroxybenzotriazole method.

  通过对五个肽片段采用叠氮法或二环己基碳二亚胺-N-羟基苯并三唑法进行组装，合成了与人类α2-纤溶酶抑制剂片段T-11的第11至26位对应的受保护十六肽酯，该片段由26个氨基酸组成，并与纤溶酶（原）赖氨酸结合位点（s）结合。