Nps-Lys(Boc)-OH | 47551-11-1

• 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: Nps-Lys(Boc)-OH
• 英文别名: N^α-<2-Nitro-phenylsulfenyl>-N^ε--L-lysin；N^α-(2-Nitrophenylthio)-N^ε-tert-butoxycarbonyl-L-Lysin；(2S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(2-nitrophenyl)sulfanylamino]hexanoic acid
• CAS: 47551-11-1
• 化学式: C₁₇H₂₅N₃O₆S
• 分子量: 399.468
• InChiKey: HOKFYJVBDQVJGZ-LBPRGKRZSA-N

物化性质

• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  159
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Nps-Lys(Boc)-OH 在 N-甲基吗啉 、 dicyclohexylammonium (2-methyl-1-indolyl)acetate 、 硫氰酸铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 38.0h， 生成 Nps-(Lys(Boc))2-4-(hydroxymethyl)benzyl 3β-cholestanyl succinate
  参考文献：
  名称：

  Potentiation of the tolerogenicity of benzylpenicilloylated eicosa-L-lysine by conjugation with 4-methoxybenzyl 3.beta.-cholestanyl succinate

  摘要：

  It was previously found that amino acid polymers such as oligolysines bearing haptenic groups in high densities efficiently suppress anti-hapten IgE antibody formation. Such conjugates are strong elicitors of anaphylaxis and therefore may not be used for desensitization of drug allergic patients. Here we report on the synthesis and immunological evaluation of benzylpenicilloylated (BPO) eicosa-L-lysines containing none, one, or two lipophilic p-(hydroxymethyl)benzyl cholestan-3 beta-yl succinate (OSuco) groups. The lipophilic derivatives suppress primary as well as ongoing anti-BPO IgE antibody formation in mice much more efficiently than their hydrophilic counterpart. The lipophilic but not the hydrophilic derivatives form stable micelles in water and suppress the antibody formation according to different cellular mechanisms. The relationship between structure, hydrophobicity, and mode of action is discussed.

  DOI：

  10.1021/jm00377a020
• 作为产物：
  描述：

  Nε-Boc-Nα-Cbz-L-赖氨酸 在 钯 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 Nps-Lys(Boc)-OH
  参考文献：
  名称：

  肽合成的新方法。二。邻硝基苯基亚磺酰基用于保护氨基的进一步实例。

  摘要：

  DOI：

  10.1021/ja01079a018

文献信息

• Selektive Spaltung substituierter Phenylsulfenyl-Schutzgruppen bei Peptidsynthesen
  作者：W. Kessler、B. Iselin

  DOI：10.1002/hlca.19660490415

  日期：——

  The selective cleavage of the N-sulphenyl protecting group from amino-acids and peptides containing additional acid-labile protecting residues has been investigated. Among various nucleophilic reagents tested for their ability to effect rapid and specific removal of the N-sulphenyl groups, hydrogen cyanide, sulfurous acid and thioacetamide have been found to be particularly suitable. The application

  已经研究了N-硫苯基保护基团从氨基酸和含有其他酸不稳定保护残基的肽上的选择性裂解。在测试其能快速和特异性去除N-硫苯基的能力的各种亲核试剂中，已经发现氰化氢，亚硫酸和硫代乙酰胺是特别合适的。描述和讨论了该方法在肽的固相合成中的应用。
• Sakarellos,C. et al., Bulletin de la Societe Chimique de France, 1976, p. 781 - 788
  作者：Sakarellos,C. et al.

  DOI：——

  日期：——
• Preparation of<i>N</i> ^α-(2-Nitrophenylthio)-<i>N</i> ^ℇ-acyl Lysine Derivatives
  作者：I. BARRAL、J. ŠAVRDA

  DOI：10.1055/s-1973-22308

  日期：——
• Potentiation of the tolerogenicity of benzylpenicilloylated eicosa-L-lysine by conjugation with 4-methoxybenzyl 3.beta.-cholestanyl succinate
  作者：Immanuel F. Luescher

  DOI：10.1021/jm00377a020

  日期：1984.11

  It was previously found that amino acid polymers such as oligolysines bearing haptenic groups in high densities efficiently suppress anti-hapten IgE antibody formation. Such conjugates are strong elicitors of anaphylaxis and therefore may not be used for desensitization of drug allergic patients. Here we report on the synthesis and immunological evaluation of benzylpenicilloylated (BPO) eicosa-L-lysines containing none, one, or two lipophilic p-(hydroxymethyl)benzyl cholestan-3 beta-yl succinate (OSuco) groups. The lipophilic derivatives suppress primary as well as ongoing anti-BPO IgE antibody formation in mice much more efficiently than their hydrophilic counterpart. The lipophilic but not the hydrophilic derivatives form stable micelles in water and suppress the antibody formation according to different cellular mechanisms. The relationship between structure, hydrophobicity, and mode of action is discussed.
• New Methods in Peptide Synthesis. II. Further Examples of the Use of the o-Nitrophenylsulfenyl Group for the Protection of Amino Groups^1,2
  作者：Leonidas Zervas、Charalambos Hamalidis

  DOI：10.1021/ja01079a018

  日期：1965.1