Boc-Trp-Pro-OMe | 85416-63-3

• 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-Trp-Pro-OMe
• 英文别名: methyl (2S)-1-[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]pyrrolidine-2-carboxylate
• CAS: 85416-63-3
• 化学式: C₂₂H₂₉N₃O₅
• 分子量: 415.489
• InChiKey: CTJQNANPSHRZGC-ROUUACIJSA-N

物化性质

• 沸点：
  636.6±55.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-Trp-Pro-OMe 在 ammonium hydroxide 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 (3S,8aS)-3-(1H-吲哚-3-基甲基)-2,3,6,7,8,8a-六氢吡咯并[2,1-f]吡嗪-1,4-二酮
  参考文献：
  名称：

  (-)-dihydrospirotryprostatin B 通过串联迈克尔加成的简明合成

  摘要：

  (-)-dihydrospirotryprostatin B ( 3 ) 是一种细胞抑制性螺[pyrrolidine-3,3'-oxindole]生物碱的不对称合成，已通过 8 个最长的线性步骤 (LLS) 从市售氨基酸中完成。合成方法的关键步骤包括二肽二酮哌嗪衍生的羟吲哚与炔酮的串联迈克尔加成，从而快速构建具有连续四元螺碳中​​心和手性的螺[吡咯烷-3,3'-羟吲哚]支架非对映选择性地建立叔胺。

  DOI：

  10.1016/j.tetlet.2021.153486
• 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 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 Boc-Trp-Pro-OMe
  参考文献：
  名称：

  l-Proline induced self-assembly of indolicidin derived palindromic tripeptide

  摘要：

  DOI：

  10.1016/j.tetlet.2014.04.090

文献信息

• Antimicrobial activity, biocompatibility and hydrogelation ability of dipeptide-based amphiphiles
  作者：Rajendra Narayan Mitra、Anshupriya Shome、Pritha Paul、Prasanta Kumar Das

  DOI：10.1039/b815368j

  日期：——

  The development of new antibiotics is of increasing importance due to the growing resistance power of microbes against conventional drugs. To this end, cationic peptides are emerging as clinically potent antimicrobial agents. In the present study, we have synthesized six dipeptide-based cationic amphiphiles with different head group structures by varying combinations of L-amino acid residues. These amphiphiles showed remarkable growth inhibiting activity on several Gram-positive (minimum inhibitory concentration (MIC) = 0.1–10 µg/mL) and Gram-negative (MIC = 5–150 µg/mL) bacteria as well as on fungus (MIC = 1–50 µg/mL). The inherent antimicrobial efficacies of these cationic dipeptides were influenced by the head group architecture of the amphiphiles. Encouragingly, these amphiphiles selectively attacked microbial cells, while showing biocompatibility toward mammalian cells. The results show that the rational designing of short peptide-based cationic amphiphiles might serve as a promising strategy in the development of antimicrobial agents with greater cell specificities. In addition, the amphiphiles showed water gelation ability at room temperature. The formation of non-covalent supramolecular networks in gelation was established by microscopic and spectroscopic studies.

  由于微生物对传统药物的耐药能力不断增强，新型抗生素的研发日益重要。为此，阳离子肽作为一种临床有效的抗菌剂正在崭露头角。在本项研究中，我们通过改变L-氨基酸残基的组合，合成了六种具有不同头部结构的双肽基阳离子两亲性分子。这些两亲性分子对多种革兰氏阳性菌（最低抑制浓度（MIC）= 0.1–10 µg/mL）、革兰氏阴性菌（MIC = 5–150 µg/mL）以及真菌（MIC = 1–50 µg/mL）显示出显著的生长抑制活性。这些阳离子双肽的固有抗菌功效受到两亲性分子头部结构的影响。令人鼓舞的是，这些两亲性分子选择性地攻击微生物细胞，同时对哺乳动物细胞表现出生物相容性。结果表明，合理设计基于短肽的阳离子两亲性分子可能是开发具有更高细胞选择性的抗菌剂的潜在策略。此外，这些两亲性分子在室温下具有水凝胶化能力。通过显微镜和光谱学研究，建立了凝胶化中非共价超分子网络的形成。
• Discovery of Dipeptide-Derived Catalysts for the Enantioselective Addition of Dimethylzinc to Aldehydes
  作者：Seock Yong Kang、Yong Sun Park

  DOI：10.1002/ejoc.201200063

  日期：2012.3

  new class of modular chiral catalysts derived from various amino acid-L-Pro dipeptides was prepared, and the catalysts were tested for their ability to catalyze the enantioselective addition of dimethylzinc to aromatic aldehydes. Dipeptides derived from L-Asp-L-Pro were identified as effective catalysts for the addition at room temperature with up to 97:3 er and 95 % yield.

  制备了一类新的模块化手性催化剂，这些催化剂来源于各种氨基酸-L-Pro 二肽，并测试了催化剂催化二甲基锌对芳香醛的对映选择性加成的能力。源自 L-Asp-L-Pro 的二肽被确定为在室温下添加的有效催化剂，效率高达 97:3，产率为 95%。
• Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-Naseseazines A and B
  作者：Madeleine E. Kieffer、Kangway V. Chuang、Sarah E. Reisman

  DOI：10.1021/ja4023557

  日期：2013.4.17

  A copper-catalyzed arylation of tryptophan derivatives is reported. The reaction proceeds with high site- and diastereoselectivity to provide aryl pyrroloindoline products in one step from simple starting materials. The utility of this transformation is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B.

  报道了色氨酸衍生物的铜催化芳基化。该反应以高位点和非对映选择性进行，从简单的起始材料一步即可提供芳基吡咯并二氢吲哚产物。这种转化的效用在天然产物 (+)-naseseazine A 和 B 的五步合成中得到了强调。
• A concise synthesis of (-)-dihydrospirotryprostatin B via tandem Michael addition
  作者：Hengqian Song、Jiacheng Song、Lihong Yan、Weigang He、Pengyan Wang、Yuanzhen Xu、Hongbo Wei、Weiqing Xie

  DOI：10.1016/j.tetlet.2021.153486

  日期：2021.11

  The asymmetric synthesis of (-)-dihydrospirotryprostatin B (3), a cytostatic spiro[pyrrolidine-3,3′-oxindole] alkaloid, has been accomplished in 8 longest linear steps (LLS) from commercially available amino acids. The key step of the synthetic approach consists of the tandem Michael addition of oxindole derived from dipeptide diketopiperazine to alkynone, leading to the rapid construction of the spiro[pyrrolidine-3

  (-)-dihydrospirotryprostatin B ( 3 ) 是一种细胞抑制性螺[pyrrolidine-3,3'-oxindole]生物碱的不对称合成，已通过 8 个最长的线性步骤 (LLS) 从市售氨基酸中完成。合成方法的关键步骤包括二肽二酮哌嗪衍生的羟吲哚与炔酮的串联迈克尔加成，从而快速构建具有连续四元螺碳中​​心和手性的螺[吡咯烷-3,3'-羟吲哚]支架非对映选择性地建立叔胺。
• Polymer-Supported Mukaiyama Reagent:  A Useful Coupling Reagent for the Synthesis of Esters and Amides
  作者：Stefano Crosignani、Jerome Gonzalez、Dominique Swinnen

  DOI：10.1021/ol0480372

  日期：2004.11.1

  Polymer-supported N-alkyl-2-chloro pyridinium triflate was synthesized in one step from Wang resin. This reagent proved to be a very effective coupling reagent for the synthesis of esters or amides from carboxylic acids and alcohols or amines (primary and secondary). [reaction: see text]

  由Wang树脂一步合成了聚合物负载的N-烷基-2-氯吡啶鎓三氟甲磺酸盐。该试剂被证明是从羧酸和醇或胺（伯和仲）合成​​酯或酰胺的非常有效的偶联剂。[反应：看文字]