N-{3-[N'-(2,7-Di-tert-butyl-9H-fluoren-9-ylmethoxycarbonyl)-hydrazinocarbonyl]-4-methoxy-phenyl}-oxalamic acid | 295800-33-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-{3-[N'-(2,7-Di-tert-butyl-9H-fluoren-9-ylmethoxycarbonyl)-hydrazinocarbonyl]-4-methoxy-phenyl}-oxalamic acid
• CAS: 295800-33-8
• 化学式: C₃₃H₃₇N₃O₇
• 分子量: 587.673
• InChiKey: XHEIFZDFFYMHGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  43.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  143.06
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-碘丁烷 、 Fmoc-L-缬氨酸 、 Fmoc-L-苯丙氨酸 、 N-{3-[N'-(2,7-Di-tert-butyl-9H-fluoren-9-ylmethoxycarbonyl)-hydrazinocarbonyl]-4-methoxy-phenyl}-oxalamic acid 、 alkaline earth salt of/the/ methylsulfuric acid 以39%的产率得到N-((S)-1-Butylcarbamoyl-2-methyl-propyl)-N'-{3-[N'-((S)-2-isobutyrylamino-3-phenyl-propionyl)-hydrazinocarbonyl]-4-methoxy-phenyl}-oxalamide
  参考文献：
  名称：

  An Unnatural Amino Acid that Mimics a Tripeptide β-Strand and Forms β-Sheetlike Hydrogen-Bonded Dimers

  摘要：

  Unnatural amino acid 2 (5-HO2CCONH-2-MeO-C6H3-CONHNH2) duplicates the hydrogen-bonding functionality of one edge of a tripeptide P-strand. It is composed of hydrazine, 5-amino-2-methoxybenzoic acid, and oxalic acid groups and is designated by the three-letter abbreviation "Hao" to reflect these three components. The 2,7-di-tert-butylfluorenylmethyloxycarbonyl (Fmoc*)- and tert-butyloxycarbonyl (Boc)-protected derivatives of Hao are prepared efficiently and in high yield by the condensation of suitably protected derivatives of hydrazine, 5-amino-2-methoxybenzoic acid, and oxalic acid. Fmoc*-Hao and Boc-Hao behave like typical Fmoc- and Boc-protected amino acids and can be incorporated into peptides by standard solid-and solution-phase peptide synthesis techniques using carbodiimide coupling agents. Hao-containing peptide 9 (i-PrCO-Phe-Hao-Val-NHBu) forms a beta-sheetlike hydrogen-bonded dimer in CDCl3 acid CD3OD-CDCl3 solutions. Peptides containing Hao and natural amino acids display hydrogen-bonding surfaces that are complementary to the hydrogen-bonding edges of protein beta-sheets.

  DOI：

  10.1021/ja001142w
• 作为产物：
  描述：

  2-Methoxy-5-nitrobenzoic acid 2-[[[2,7-bis(1,1-dimethylethyl)-9H-fluoren-9-yl]methoxy]carbonyl]hydrazide 在 10percent Pd/C 吡啶 、 sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.75h， 生成 N-{3-[N'-(2,7-Di-tert-butyl-9H-fluoren-9-ylmethoxycarbonyl)-hydrazinocarbonyl]-4-methoxy-phenyl}-oxalamic acid
  参考文献：
  名称：

  An Unnatural Amino Acid that Mimics a Tripeptide β-Strand and Forms β-Sheetlike Hydrogen-Bonded Dimers

  摘要：

  Unnatural amino acid 2 (5-HO2CCONH-2-MeO-C6H3-CONHNH2) duplicates the hydrogen-bonding functionality of one edge of a tripeptide P-strand. It is composed of hydrazine, 5-amino-2-methoxybenzoic acid, and oxalic acid groups and is designated by the three-letter abbreviation "Hao" to reflect these three components. The 2,7-di-tert-butylfluorenylmethyloxycarbonyl (Fmoc*)- and tert-butyloxycarbonyl (Boc)-protected derivatives of Hao are prepared efficiently and in high yield by the condensation of suitably protected derivatives of hydrazine, 5-amino-2-methoxybenzoic acid, and oxalic acid. Fmoc*-Hao and Boc-Hao behave like typical Fmoc- and Boc-protected amino acids and can be incorporated into peptides by standard solid-and solution-phase peptide synthesis techniques using carbodiimide coupling agents. Hao-containing peptide 9 (i-PrCO-Phe-Hao-Val-NHBu) forms a beta-sheetlike hydrogen-bonded dimer in CDCl3 acid CD3OD-CDCl3 solutions. Peptides containing Hao and natural amino acids display hydrogen-bonding surfaces that are complementary to the hydrogen-bonding edges of protein beta-sheets.

  DOI：

  10.1021/ja001142w

文献信息

• Macrocyclic β-Sheet Peptides That Mimic Protein Quaternary Structure through Intermolecular β-Sheet Interactions
  作者：Omid Khakshoor、Borries Demeler、James S. Nowick

  DOI：10.1021/ja068511u

  日期：2007.5.1

  of cyclic peptides that mimic protein quaternary structure through β-sheet interactions. These peptides are 54-membered-ring macrocycles comprising an extended heptapeptide β-strand, two Hao β-strand mimics [JACS 2000, 122, 7654] joined by one additional α-amino acid, and two δ-linked ornithine β-turn mimics [JACS 2003, 125, 876]. Peptide 3a, as the representative of these cyclic peptides, contains

  本文报道了通过 β-折叠相互作用模拟蛋白质四级结构的环肽家族的设计、合成和表征。这些肽是 54 元环大环化合物，包含一条延伸的七肽 β-链、两个由一个额外的 α-氨基酸连接的Hao β-链模拟物 [JACS 2000, 122, 7654] 和两个 δ-连接的鸟氨酸 β-转角模拟物[JACS 2003, 125, 876]。肽3a作为这些环肽的代表，包含改编自蛋白质NuG2的二聚化界面的七肽序列（TSFTYTS）[PDB ID：1mio]。肽 3a 水溶液的 1 H NMR 研究表明，部分折叠的单体与强折叠的寡聚物缓慢交换。NOE 研究清楚地表明，肽通过边对边 β-片层二聚化进行自缔合。脉冲场梯度 (PFG) NMR 扩散系数测量和分析超速离心 (AUC) 研究确定该低聚物是四聚物。总的来说，这些实验表明...