N’-Boc-L-tryptophan benzyl ester | 1170940-54-1

• 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: N’-Boc-L-tryptophan benzyl ester
• 英文别名: H-L-Trp(Boc)-OBn；H-Trp(Boc)-OBn；tert-butyl 3-[(2S)-2-amino-3-oxo-3-phenylmethoxypropyl]indole-1-carboxylate
• CAS: 1170940-54-1
• 化学式: C₂₃H₂₆N₂O₄
• 分子量: 394.47
• InChiKey: OXWGNFQHUJLCGO-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N’-Boc-L-tryptophan benzyl ester 在 二(三苯基膦)环戊二烯基氯化钌(II) 、 imidazole-1-sulfonyl azide dihydrochloride 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 Fmoc-Gly ψ[1,5-Tz]Trp(Boc)-OBn
  参考文献：
  名称：

  1,5-Disubstituted 1,2,3-Triazoles as Amide Bond Isosteres Yield Novel Tumor-Targeting Minigastrin Analogs

  摘要：

  DOI：

  10.1021/acsmedchemlett.0c00636
• 作为产物：
  描述：

  Fmoc-L-色氨酸(Boc)-OH 在 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 N’-Boc-L-tryptophan benzyl ester
  参考文献：
  名称：

  1,5-Disubstituted 1,2,3-Triazoles as Amide Bond Isosteres Yield Novel Tumor-Targeting Minigastrin Analogs

  摘要：

  DOI：

  10.1021/acsmedchemlett.0c00636

文献信息

• Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis
  作者：Débora Munhoz Rodrigues、Gisele Bulhões Portapilla、Guilherme Martins Silva、Andressa Duarte、Cristiana Gonçalez Rotta、Carlos Henrique Tomich de Paula da Silva、Sérgio de Albuquerque、Jairo Kenupp Bastos、Vanessa Leiria Campo

  DOI：10.1016/j.bmc.2021.116372

  日期：2021.10

  have antitumor activities and can selectively inhibit the AKR1C3 enzyme, overexpressed in hormone-dependent prostate and breast tumors. Thus, in an attempt to develop new cytotoxic inhibitors against these cancers, three prenylated compounds, artepillin C, drupanin and baccharin, were isolated from green propolis to synthesize new derivatives via coupling reactions with different amino acids. All obtained

  乳腺癌在女性中的发病率和死亡率最高，而前列腺癌在男性中的发病率第二高。研究表明，巴西绿蜂胶中的化合物具有抗肿瘤活性，可以选择性地抑制在激素依赖性前列腺和乳腺肿瘤中过度表达的 AKR1C3 酶。因此，为了开发针对这些癌症的新细胞毒抑制剂，从绿蜂胶中分离出三种异戊二烯化化合物，青蒿素 C、drupanin 和 baccharin，通过与不同氨基酸的偶联反应合成新的衍生物。所有获得的衍生物都进行了针对四种癌细胞（MCF-7、MDA MB-231、PC-3 和 DU145）和两种正常细胞系（MCF-10A 和 PNT-2）的抗增殖试验，以评估它们的细胞毒性。一般来说，观察到化合物的最佳活性 如图6e所示，衍生自drupanin，其对MCF-7细胞的半数最大抑制浓度(IC 50 )为9.6 ± 3 μM，选择性指数(SI)为5.5。 计算机 研究表明，这些衍生物呈现出针对 AKR1C3 的连贯对接相互作用和结合模式，这可能代表了
• Synthesis of Carbohydrate-Templated Amino Acids and Methods of Using Same
  申请人：Schweizer Frank

  公开号：US20080275213A1

  公开（公告）日：2008-11-06

  The present invention generally relates to tetrahydropyranyl-derivatized amino acids, their syntheses and their incorporation into peptides and peptidomimetics. The tetrahydropyran moiety constrains the side chain of an amino acid, thereby providing a molecule that may act as a sugar- or amino acid-mimetic as well as a scaffold for combinatorial synthesis.

  这项发明通常涉及四氢吡喃基衍生的氨基酸，它们的合成以及它们被纳入肽和肽类似物中。四氢吡喃基约束氨基酸的侧链，从而提供一种可能作为糖或氨基酸类似物的分子，同时也作为组合合成的支架。
• Synthesis of glucose-templated lysine analogs and incorporation into the antimicrobial dipeptide sequence kW-OBn
  作者：Kaidong Zhang、Dhananjoy Mondal、George G. Zhanel、Frank Schweizer

  DOI：10.1016/j.carres.2008.04.018

  日期：2008.7

  The synthesis of two glucose-templated (GlcT) lysine analogs GlcTK and GlcTk in which the side chain of D- and L-lysine (k and K) is conformationally constrained via incorporation into a D-glucose scaffold is described. A key-step in the synthesis is a high yielding, reductive ring opening of an exocyclic glucose-derived epoxide to form a alpha-hydroxy ester that can be converted into GlcTK and GlcTk

  描述了两个葡萄糖模板化的（GlcT）赖氨酸类似物GlcTK和GlcTk的合成，其中D-和L-赖氨酸（k和K）的侧链通过掺入D-葡萄糖支架而在构象上受到约束。合成中的关键步骤是高产量的环外葡萄糖衍生的环氧化物的还原环开环反应，以形成可转化为GlcTK和GlcTk的α-羟基酯。为了证明在肽合成中使用这些构件，我们在抗菌二肽序列kW-OBn（W = L-色氨酸）中替换了D-赖氨酸，并确定了对各种革兰氏阳性和革兰氏阴性生物的抗菌活性。我们的结果表明，二肽kW-OBn中未保护的GlcTk取代D-赖氨酸会导致抗菌活性降低。
• Synthesis and antibacterial activity of amphiphilic lysine-ligated neomycin B conjugates
  作者：Smritilekha Bera、George G. Zhanel、Frank Schweizer

  DOI：10.1016/j.carres.2011.01.015

  日期：2011.4

  Amphiphilic lysine-ligated neomycin B building blocks were prepared by reductive amination of a protected C5 ''-modified neomycin B-based aldehyde and side chain-unprotected lysine or lysine-containing peptides. It was demonstrated that a suitably protected lysine-ligated neomycin B conjugate (NeoK) serves as a building block for peptide synthesis, enabling incorporation of aminoglycoside binding sites into peptides. Antibacterial testing of three amphiphilic lysine-ligated neomycin B conjugates against a representative panel of Gram-positive and Gram-negative strains demonstrates that C5 ''-modified neomycin-lysine conjugate retains antibacterial activity. However, in most cases the lysine-ligated neomycin B analogs display reduced potency against Gram-positive strains when compared to unmodified neomycin B or unligated peptide. An exception is MRSA where an eightfold enhancement was observed. When compared to unmodified neomycin B, the prepared lysine-neomycin conjugates exhibited a 4-8-fold enhanced Gram-negative activity against Pseudomonas aeruginosa and up to 12-fold enhanced activity was observed when compared to unligated reference peptides. (C) 2011 Elsevier Ltd. All rights reserved.
• 1,5-Disubstituted 1,2,3-Triazoles as Amide Bond Isosteres Yield Novel Tumor-Targeting Minigastrin Analogs
  作者：Nathalie M. Grob、Roger Schibli、Martin Béhé、Ibai E. Valverde、Thomas L. Mindt

  DOI：10.1021/acsmedchemlett.0c00636

  日期：2021.4.8