BOC-L-高酪氨酸 | 198473-94-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 酪氨酸类衍生物
• 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
• 中文名称: BOC-L-高酪氨酸
• 中文别名: Boc-高酪氨酸
• 英文名称: Boc-hTyr
• 英文别名: N-Boc-L-homotyrosine；Boc-homo-L-tyrosine；(2S)-4-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 198473-94-8
• 化学式: C₁₅H₂₁NO₅
• mdl: MFCD03095573
• 分子量: 295.335
• InChiKey: CDPGKTTZDRPESV-LBPRGKRZSA-N

物化性质

• 沸点：
  495.3±40.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.466
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  BOC-L-高酪氨酸 在 TEA 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (S)-2-tert-Butoxycarbonylamino-4-(4-trifluoromethanesulfonyloxy-phenyl)-butyric acid benzyl ester
  参考文献：
  名称：

  环状氨基六肽的全合成和抗真菌评估。

  摘要：

  对治疗全身性真菌感染的新疗法的需求持续增长。天然存在的六肽棘皮菌素B（1）通过抑制β-1,3葡聚糖（一种重要的真菌细胞壁成分）的合成，显示出强大的抗真菌活性。尽管到目前为止，由于该试剂的理化特性而受到限制，但我们发现在“西北”位置带有氨基脯氨酸残基的类似物的合成可大大改善水溶性（> 5 mg / mL）。报道了基于整个细胞和一系列化合物的体内活性的合成和构效关系（SAR）。

  DOI：

  10.1016/s0968-0896(00)00097-3

文献信息

• Renin Inhibitors
  申请人：Baldwin John J.

  公开号：US20100317697A1

  公开（公告）日：2010-12-16

  Disclosed are compounds having the formula (I): wherein the R 1 , R 2 , R 3 , X, Y, A, L, and G are defined herein. These compounds bind to aspartic proteases to inhibit their activity and are useful in the treatment or amelioration of diseases associated with aspartic protease activity. Also disclosed are methods of use of the compounds of Formula I for ameliorating or treating aspartic protease related disorders in a subject in need thereof.

  揭示了具有以下化学式(I)的化合物：其中R1、R2、R3、X、Y、A、L和G在此处被定义。这些化合物结合到天冬氨酸蛋白酶上以抑制其活性，并且在治疗或改善与天冬氨酸蛋白酶活性相关的疾病中很有用。还揭示了使用化合物I的方法，用于改善或治疗需要的患有天冬氨酸蛋白酶相关疾病的受试者。
• Inhibitor of apoptosis protein (IAP) antagonists
  申请人：Sanford Burnham Prebys Medical Discovery Institute

  公开号：US10544188B2

  公开（公告）日：2020-01-28

  Provided herein are compounds that modulate the activity of inhibitor of apoptosis proteins (IAPs), compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

  本文提供了调节细胞凋亡抑制蛋白（IAPs）活性的化合物、包含这些化合物的组合物以及使用这些化合物和包含这些化合物的组合物的方法。
• Broad spectrum antiviral compounds
  申请人：University of Southern California

  公开号：US10919922B2

  公开（公告）日：2021-02-16

  Antiviral compounds comprising prodrugs with differing side chains derived from a tyrosine substance in the form of a tyrosine amide in which the amide substituent side chain is an alkyl ether, thioether, or alkene. Embodiments of the compounds have a range of effective lipophilicity values allowing variation in aqueous solubility, oral bioavailability, cell permeability and in vivo activation properties. The embodiments have promoieties derived from a single amino acid, which are expected to have low toxicity. The features described above also make possible a novel “precision medicine” approach to treatment of viral infections, whereby the prodrug variations can be exploited to match optimal activation of the prodrug to a given patient or strain of virus.

  抗病毒化合物包括具有不同侧链的原药，这些侧链来源于酪氨酸物质，其形式为酪氨酸酰胺，其中酰胺取代侧链为烷基醚、硫醚或烯。本发明化合物的实施方案具有一定范围的有效亲脂性值，可使水溶性、口服生物利用度、细胞渗透性和体内活化特性发生变化。本发明的实施例具有源自单一氨基酸的原基，预计毒性较低。上述特点还使一种治疗病毒感染的新型 "精准医疗 "方法成为可能，即可以利用原药的变化，使原药的最佳活化与特定患者或病毒株相匹配。
• Total synthesis and structure–activity relationships of new echinocandin-like antifungal cyclolipohexapeptides
  作者：Jianzhong Yao、Hongming Liu、Ting Zhou、Hai Chen、Zhenyuan Miao、Chunquan Sheng、Wannian Zhang

  DOI：10.1016/j.ejmech.2012.01.054

  日期：2012.4

  A series of new echinocandin-like cyclolipohexapeptides were designed and total synthesized via solution phase [3 + 3]-segment coupling strategy with an attempt to improve antifungal activity. The designed compounds showed potent antifungal activities with broad spectrum. In particular, 11 compounds (i.e. 28a-e, 28g, 28i-j, 29a, 29c and 29e) showed better in vitro antifungal activities against Candida albicans or Aspergillus fumigatus than caspofungin. Moreover, the synthesized compounds provided new SAR information for the echinocandins. The findings in this work suggested that the "left" tripeptide segment of cyclolipohexapeptide scaffold might be a hydrophilic structural motif, whereas the "right" lipopeptide segment was preferred as a hydrophobic core. The amino acid component of the cyclolipohexapeptide scaffold could significantly affect the SAR of the side chains. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Influence of azide incorporation on binding affinity by small papain inhibitors
  作者：Angelique E.M. Wammes、Tom G. Hendriks、Helene I.V. Amatdjais-Groenen、Marloes A. Wijdeven、Jan C.M. van Hest、Floris L. van Delft、Tina Ritschel、Floris P.J.T. Rutjes

  DOI：10.1016/j.bmc.2014.06.001

  日期：2014.10

  In order to develop affinity-based biosensor platforms, appropriate ligands with a functional handle for immobilization onto a biosensor surface are required. To this end, a library of papain inhibitors was designed and synthesized, containing different azide linkers for subsequent immobilization by 'click' chemistry, in this particular case by copper-free, strain-promoted azide-alkyne cycloaddition (SPAAC). Furthermore, a molecular docking study was performed to obtain a better insight as to at which position such azide handles could be tolerated without affecting binding affinity. Although the azide moiety is small, in some cases its introduction strongly influenced the binding affinity. For one class of inhibitors a swapped binding mode was proposed to explain the results. In addition, a specific site for linker introduction was identified, which did not significantly affect the binding affinity. (C) 2014 Elsevier Ltd. All rights reserved.