Boc-Gln-Val-OPac | 151782-02-4

• 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-Gln-Val-OPac
• 英文别名: Boc-Gln-Val-OPa；Boc-Gln-Val-OGly-Ph；phenacyl (2S)-2-[[(2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoyl]amino]-3-methylbutanoate
• CAS: 151782-02-4
• 化学式: C₂₃H₃₃N₃O₇
• 分子量: 463.531
• InChiKey: JJKLDNUBCGYSPW-LPHOPBHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  154
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-Gln-Val-OPac 在 锌 溶剂黄146 作用下， 生成 N-(N-(1,1-dimethylethoxycarbonyl)-L-glutaminyl)-L-valine
  参考文献：
  名称：

  Design of the Synthetic Route for Peptides and Proteins Based on the Solubility Prediction Method. I. Synthesis and Solubility Properties of Human Proinsulin C-Peptide Fragments

  摘要：

  利用相对较小的人类胰岛素原C肽片段，展示了溶解度预测方法的实用性。还从以下方面考察了该溶解度预测方法对于含有极性侧链肽的适用性：（1）小于七肽的肽中间体具有高溶解性，与其值无关；（2）肽中间体的值有助于判断等于或大于八肽水平的肽中间体的溶解度；（3）肽链中央位置的Pro残基能有效提高肽的溶解度；（4）存在导致β折叠聚集体引起的不溶性的临界链长度。随后，在肽中间体溶解度预测的基础上，讨论了适用于人胰岛素原C肽合成路线设计的策略。

  DOI：

  10.1246/bcsj.59.2433
• 作为产物：
  描述：

  2-oxo-2-phenylethyl (tert-butoxycarbonyl)-L-valinate 在 N-甲基吗啉 、 盐酸 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 4.5h， 生成 Boc-Gln-Val-OPac
  参考文献：
  名称：

  Design of the Synthetic Route for Peptides and Proteins Based on the Solubility Prediction Method. I. Synthesis and Solubility Properties of Human Proinsulin C-Peptide Fragments

  摘要：

  利用相对较小的人类胰岛素原C肽片段，展示了溶解度预测方法的实用性。还从以下方面考察了该溶解度预测方法对于含有极性侧链肽的适用性：（1）小于七肽的肽中间体具有高溶解性，与其值无关；（2）肽中间体的值有助于判断等于或大于八肽水平的肽中间体的溶解度；（3）肽链中央位置的Pro残基能有效提高肽的溶解度；（4）存在导致β折叠聚集体引起的不溶性的临界链长度。随后，在肽中间体溶解度预测的基础上，讨论了适用于人胰岛素原C肽合成路线设计的策略。

  DOI：

  10.1246/bcsj.59.2433

文献信息

• Studies of the synthesis, immunology, and cytotoxicity of a cyclic octapeptide corresponding to TNF-.alpha.-(59-66)
  作者：Leung Sheh、Hsou Hung Lin、Kee Ching G. Jeng、Chia Fu Chen

  DOI：10.1021/jm00078a020

  日期：1993.12

  In an attempt to investigate possible binding domains of the tumor necrosis factors (TNF), we have previously synthesized a cyclic hexapeptide corresponding to murine TNF-(127-132) (cTNF-1).(3) In this report, we describe the synthesis and biological activity of another cyclic octapeptide corresponding to human TNF-alpha-(59-66) (cTNF-2). The design of these cyclic peptides is based on their high sequence homology with corresponding fragments of human TNF-alpha or TNF-beta. Similar to cTNF-1,(3) the cyclic octapeptide cTNF-2 displayed low in vitro cytotoxicity against human HeLa and HEP-2 cell lines. The cyclic peptides cTNF-2 and cTNF-1 were then tested for the induction of interleukin-l (IL-1) production from human peripheral blood mononuclear cells and monocytes in vitro. At low concentrations, the IL-1 levels induced by these cyclic peptides were similar to that of recombinant TNF-alpha. However, the IL-1 production by cTNF-2 stimulation was dose-dependently increased and reached that of a lipopolysaccharide (LPS; 0.1 mu g/mL) level. These findings suggest that the fragments corresponding to human TNF-alpha-(59-66) and murine TNF-(127-132) may represent certain binding domains of the tumor necrosis factors that elicit IL-1 production.
• Design of the Synthetic Route for Peptides and Proteins Based on the Solubility Prediction Method. I. Synthesis and Solubility Properties of Human Proinsulin C-Peptide Fragments
  作者：Mitsuaki Narita、Toshihiko Ogura、Kazuhiro Sato、Shinya Honda

  DOI：10.1246/bcsj.59.2433

  日期：1986.8

  The usefulness of the solubility prediction method is demonstrated using relatively small peptide fragments of human proinsulin C-peptide. The propriety of the solubility prediction method for peptides having polar side chains is also examined in the following respects: (1) Peptide intermediates smaller than a heptapeptide have high solubility regardless of their values; (2) the values of peptide intermediates are useful for judging solubility of peptide intermediates equal to or larger than an octapeptide level; (3) the Pro residue in a central position of a peptide chain is effective for increasing peptide solubility; and (4) there is critical chain length for peptide insolubility caused by a β-sheet aggregation. A strategy suitable for the design of the synthetic route for human proinsulin C-peptide is subsequently discussed on the basis of the solubility prediction of peptide intermediates.

  利用相对较小的人类胰岛素原C肽片段，展示了溶解度预测方法的实用性。还从以下方面考察了该溶解度预测方法对于含有极性侧链肽的适用性：（1）小于七肽的肽中间体具有高溶解性，与其值无关；（2）肽中间体的值有助于判断等于或大于八肽水平的肽中间体的溶解度；（3）肽链中央位置的Pro残基能有效提高肽的溶解度；（4）存在导致β折叠聚集体引起的不溶性的临界链长度。随后，在肽中间体溶解度预测的基础上，讨论了适用于人胰岛素原C肽合成路线设计的策略。