Boc-Tyr-Pro-OMe | 82609-80-1

• 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-OMe
• 英文别名: Boc-L-Tyr-L-Pro-OMe；Methyl (tert-butoxycarbonyl)-L-tyrosyl-L-prolinate；methyl (2S)-1-[(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]pyrrolidine-2-carboxylate
• CAS: 82609-80-1
• 化学式: C₂₀H₂₈N₂O₆
• 分子量: 392.452
• InChiKey: CVMPNBVSNFLXBL-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Tyr-Pro-OMe 以 水 为溶剂， 反应 4.0h， 以84%的产率得到环(脯氨酸一酪氨酸)
  参考文献：
  名称：

  An efficient green synthesis of proline-based cyclic dipeptides under water-mediated catalyst-free conditions

  摘要：

  L-Proline-based cyclic dipeptides were synthesized from N-Boc-protected dipeptide methyl esters under catalyst-free condition using water as a solvent. One-pot deprotection and cyclization have been used is the key steps, providing an efficient and environmentally friendly approach. Clean reaction conditions, easy isolation, and good yields of cyclic dipeptides are the salient features of the proposed methodology (C) 2010 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.134
• 作为产物：
  描述：

  Boc-L-酪氨酸 、 L-脯氨酸甲酯盐酸盐 在 N,N'-二环己基碳二亚胺 作用下， 生成 Boc-Tyr-Pro-OMe
  参考文献：
  名称：

  Synthesis, Cytotoxic and Antimicrobial Screening of a Proline-Rich Cyclopolypeptide

  摘要：

  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。

  DOI：

  10.1248/cpb.57.214

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。
• Opioid Activities of Morphiceptin Analogs Derived from Human β-Casein
  作者：Kazuyasu Sakaguchi、Hiroshi Sakamoto、Yoshiko Tsubaki、Michinori Waki、Tommaso Costa、Yasuyuki Shimohigashi

  DOI：10.1246/bcsj.63.1753

  日期：1990.6

  Four tetrapeptide amides with the N-terminal Tyr–Pro sequence were synthesized as possible opioid agonists that can be produced by degradation of human β-casein. When these peptides were tested for their ability to bind to the μ and δ opioid receptors in rat brain, only H–Tyr–Pro–Phe–Val-NH2 was active, showing the 60% increased affinity for the μ receptors as compared with morphiceptin (H–Tyr–Pro–Phe–Pro–NH2) derived from bovine β-casein. It was highly μ-selective, as well as morphiceptin, with the μ/δ-selectivity ratio of 285. Other three analogs, H–Tyr–Pro–Ser–Phe–NH2, H–Tyr–Pro–Val–Arg–NH2 and H–Tyr–Pro–Val–Pro–NH2, were almost completely inactive. These results suggested that, for the morphiceptin-like tetrapeptide amides, the presence of Phe at position 3 is essential to elicit an activity to bind to the μ opioid receptors. Conformational considerations by measuring the CD spectra indicated that the sequence of tetrapeptide amide Tyr–Pro–Xxx–Pro(or Val)–NH2 is an important structural requirement to interact with the μ opioid receptors.

  合成了四种含有N端Tyr–Pro序列的四肽酰胺，它们可能是由人β-酪蛋白降解产生的可能与阿片受体结合的物质。当这些肽用于测试它们结合大鼠脑μ和δ阿片受体的能力时，仅H–Tyr–Pro–Phe–Val-NH2有活性，与来自牛β-酪蛋白的吗啡酰肽(H–Tyr–Pro–Phe–Pro–NH2)相比，它对μ受体具有60%的亲和力增加。它也像吗啡酰肽一样具有很高的μ选择性，μ/δ选择性比为285。其他三个类似物，H–Tyr–Pro–Ser–Phe–NH2、H–Tyr–Pro–Val–Arg–NH2 和 H–Tyr–Pro–Val–Pro–NH2，几乎完全无活性。这些结果表明，对于类似吗啡酰肽的四肽酰胺，在第3位存在Phe对于引发与μ阿片受体的结合活性至关重要。通过测量圆二色谱光谱进行的构象分析表明，四肽酰胺序列 Tyr–Pro–Xxx–Pro(或Val)–NH2 是与μ阿片受体相互作用的重要结构要求。
• Ru‐Catalyzed C−H Hydroxylation of Tyrosine‐Containing Di‐ and Tripeptides toward the Assembly of L‐DOPA Derivatives
  作者：Paula Andrade‐Sampedro、Jon M. Matxain、Arkaitz Correa

  DOI：10.1002/adsc.202200234

  日期：2022.6.21

  C(sp2)−H hydroxylation of a collection of Tyr-containing di- and tripeptides featuring the use of a carbamate as a removable directing group and PhI(OCOCF3)2 (PIFA) as oxidant. This air-compatible tagging technique is reliable, scalable and provides access to L-DOPA (L-3,4-dihydroxyphenylalanine) peptidomimetics in a racemization-free fashion. Density Functional Theory calculations support a Ru(II)/Ru(IV)

  开发用于肽框架内氨基酸后期修饰的催化工具是一项至关重要的具有挑战性的任务。在此，我们报道了一系列含 Tyr 的二肽和三肽的 Ru 催化 C( sp 2 )-H 羟基化反应，其特点是使用氨基甲酸酯作为可去除的导向基团和 PhI(OCOCF 3 ) 2 (PIFA) 作为氧化剂. 这种与空气兼容的标记技术可靠、可扩展，并以无消旋的方式提供对 L-DOPA（L-3,4-二羟基苯丙氨酸）肽模拟物的访问。密度泛函理论计算支持 Ru(II)/Ru(IV) 催化循环。
• A New Oxyma Derivative for Nonracemizable Amide-Forming Reactions in Water
  作者：Qinghui Wang、Yong Wang、Michio Kurosu

  DOI：10.1021/ol3013556

  日期：2012.7.6

  An Oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (2), displayed remarkable physicochemical properties as a peptide-coupling additive for peptide-forming reactions in water. Short peptides to oligopeptides could be synthesized by using 2, EDCI, and NaHCO3 in water without measurable racemization. Significantly, a simple basic and acidic aqueous workup procedure can remove all reagents utilized in the reactions to afford only coupling products in consistently excellent yields.