Boc-Ada²-Ala(Bzl₂) | 134653-44-4

• 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-Ada²-Ala(Bzl₂)
• 英文别名: (2S)-2-[[(2S)-4-[bis(2-oxo-2-phenylmethoxyethyl)amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]propanoic acid
• CAS: 134653-44-4
• 化学式: C₃₀H₃₉N₃O₉
• 分子量: 585.654
• InChiKey: XBQIIMJNEIKCID-URXFXBBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  160.57
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  (2S)-N²-Boc-N⁴-Fmoc-2,4-diamino-1-butanol 在 哌啶 、 sodium dichromate 、 硫酸 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 、 焦碳酸二乙酯 、 三氟乙酸 、 sodium iodide 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 31.5h， 生成 Boc-Ada²-Ala(Bzl₂)
  参考文献：
  名称：

  Synthesis of peptides containing unnatural, metal-ligating residues: aminodiacetic acid as a peptide side chain

  摘要：

  Peptides possessing a pair of residues separated by one turn in the alpha-helical conformation and potentially capable of ligating a single metal ion in aqueous solution were designed. It was predicted that the resulting cross-link would shift toward alpha-helix the random coil/alpha-helix equilibrium. The syntheses of 10 peptides Ac-Ada(l)Ala(m)Ada(l)(Ala4GluLys)n-NH2 where Ada(l) is an L-alpha-amino acid residue with an aminodiacetic acid bearing side chain, -(CH2)(l)N(CH2CO2H)2 (with values of l, m, and n as follows: 1, 2, 3 (1); 1, 3, 1 (2a); 1, 3, 2 (2b); 1, 3, 3 (2c); 2, 2, 3 (3); 2, 3, 3 (4); 3, 2, 3 (5); 3, 3, 3 (6); 4, 2, 3 (7); 4, 3, 3 (8)) are described using Boc chemistry on p-methylbenzhydrylamine resin. The aminodiacetic acid bearing residues were incorporated with side chains protected as the dibenzyl esters. To avoid side reactions, residues Ada(l) for l = 1 and 2 were incorporated by a block approach. Peptide structures were confirmed by observation of the predicted parent ions in the FAB MS. The circular dichroism spectra of several of these peptides that posses a pair of metal-ligating residues separated by two or three intervening residues have previously been shown to undergo changes on addition of metal ions consistent with appreciable enhancement of helix content.

  DOI：

  10.1021/jo00014a006

文献信息

• RUAN, FUQIANG;CHEN, YANQIU;ITOH, KATSUMI;SASAKI, TOMIKAZU;HOPKINS, PAUL B+, J. ORG. CHEM., 56,(1991) N4, C. 4347-4354
  作者：RUAN, FUQIANG、CHEN, YANQIU、ITOH, KATSUMI、SASAKI, TOMIKAZU、HOPKINS, PAUL B+

  DOI：——

  日期：——