benzyl 2S-(6-tert-butoxycarbonylamino)-1-(methoxy-1-oxohexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate | 112920-78-2

• 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: benzyl 2S-(6-tert-butoxycarbonylamino)-1-(methoxy-1-oxohexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate
• 英文别名: Z-Pro-Lys(Boc)-OMe
• CAS: 112920-78-2
• 化学式: C₂₅H₃₇N₃O₇
• 分子量: 491.585
• InChiKey: OKSSJAZCFBCQGM-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  123.27
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  benzyl 2S-(6-tert-butoxycarbonylamino)-1-(methoxy-1-oxohexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 6.25h， 生成 Z-Arg(Adoc)2-Pro-Lys(Boc)
  参考文献：
  名称：

  Franzen, Henry M.; Ragnarsson, Ulf; Nagren, Kjell, Journal of the Chemical Society. Perkin transactions I, 1987, p. 2241 - 2248

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate 、 N-苄氧羰基-L-脯氨酸 N-羟基琥珀酰亚胺酯 以 二氯甲烷 为溶剂， 以93%的产率得到benzyl 2S-(6-tert-butoxycarbonylamino)-1-(methoxy-1-oxohexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Franzen, Henry M.; Ragnarsson, Ulf; Nagren, Kjell, Journal of the Chemical Society. Perkin transactions I, 1987, p. 2241 - 2248

  摘要：

  DOI：

文献信息

• Introducing Savie: A Biodegradable Surfactant Enabling Chemo- and Biocatalysis and Related Reactions in Recyclable Water
  作者：Joseph R. A. Kincaid、Madison J. Wong、Nnamdi Akporji、Fabrice Gallou、David M. Fialho、Bruce H. Lipshutz

  DOI：10.1021/jacs.2c13444

  日期：——

  organic synthesis in recyclable water. This includes homogeneous catalysis (including examples employing only ppm levels of catalyst), heterogeneous catalysis, and biocatalytic transformations, including a multistep chemoenzymatic sequence. Use of Savie frequently leads to significantly higher yields than do conventional surfactants, while obviating the need for waste-generating organic solvents.

  Savie 是一种可生物降解的表面活性剂，源自维生素 E 和聚肌氨酸 (PSar)，开发用于可循环水中的有机合成。这包括均相催化（包括仅使用 ppm 级催化剂的例子）、多相催化和生物催化转化，包括多步化学酶序列。使用 Savie 通常会比传统表面活性剂产生显着更高的产率，同时无需使用产生废物的有机溶剂。
• Vinyl Sulfone-Based Peptidomimetics as Anti-Trypanosomal Agents: Design, Synthesis, Biological and Computational Evaluation
  作者：Elizabeth Dunny、William Doherty、Paul Evans、J. Paul G. Malthouse、Derek Nolan、Andrew J. S. Knox

  DOI：10.1021/jm400294w

  日期：2013.9.12

  A series of vinyl sulfone-containing peptidomimetics were rationally designed, synthesized, and evaluated against Trypanosoma brucei brucei. These electrophilic compounds are likely to exert their antitrypanosomal activity via inhibition of trypanosomal cysteine proteases, TbCatB and rhodesain, through alkylation of a key cysteine residue Within the protease active site. The series was designed to present complementary groups to naturally recognized peptide substrates while probing tolerance to a range of substitutions at the PI, P1', and P2 positions. The most potent compound, 29 (EC50 = 70 nM, T. b. brucei whole cell assay), displayed minimal toxicity (>785 times Selectivity) when assayed for cytotoxicity against the human promyelocytic leukemia (HL-60) cell line. Cells treated with compound 29, as with K777 (2), exhibited an increase in both the number of multinucleated cells and cells with swollen flagellar pockets. Computational analysis revealed a strong correlation between the hypothetical binding mode in TbCatB/rhodesain and trypanocidal activity in vitro.