(2S)-N²-Boc-N⁴-Fmoc-2,4-diamino-1-butanol | 134653-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S)-N²-Boc-N⁴-Fmoc-2,4-diamino-1-butanol
• 英文别名: tert-butyl N-[(2S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-1-hydroxybutan-2-yl]carbamate
• CAS: 134653-33-1
• 化学式: C₂₄H₃₀N₂O₅
• 分子量: 426.513
• InChiKey: LWQBFCVSKKPOTC-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  96.89
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S)-N²-Boc-N⁴-Fmoc-2,4-diamino-1-butanol 在 三氧化硫吡啶 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 {(S)-1-Formyl-3-[methyl-(2,2,2-trifluoro-acetyl)-amino]-propyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Exploration of the P1 SAR of aldehyde cathepsin K inhibitors

  摘要：

  The synthesis and biological activity of a series of aldehyde inhibitors of cathepsin K are reported. Exploration of the properties of the S(1) subsite with a series of alpha-amino aldehyde derivatives substituted at the P(1) position afforded compounds with cathepsin K IC(50)s between 52 microM and 15 nM.

  DOI：

  10.1016/j.bmcl.2003.09.088
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 生成 (2S)-N²-Boc-N⁴-Fmoc-2,4-diamino-1-butanol
  参考文献：
  名称：

  Exploration of the P1 SAR of aldehyde cathepsin K inhibitors

  摘要：

  The synthesis and biological activity of a series of aldehyde inhibitors of cathepsin K are reported. Exploration of the properties of the S(1) subsite with a series of alpha-amino aldehyde derivatives substituted at the P(1) position afforded compounds with cathepsin K IC(50)s between 52 microM and 15 nM.

  DOI：

  10.1016/j.bmcl.2003.09.088

文献信息

• Synthesis of peptides containing unnatural, metal-ligating residues: aminodiacetic acid as a peptide side chain
  作者：Fuqiang Ruan、Yanqiu Chen、Katsumi Itoh、Tomikazu Sasaki、Paul B. Hopkins

  DOI：10.1021/jo00014a006

  日期：1991.7

  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.