Gly-OTSE | 58083-00-4

• 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: Gly-OTSE
• CAS: 58083-00-4
• 化学式: C₁₁H₁₅NO₄S
• 分子量: 257.31
• InChiKey: CMZCFLHUJWWXPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  86.46
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  BOC-Gly-OTSE 在 盐酸 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 生成 Gly-OTSE
  参考文献：
  名称：

  [激素-受体相互作用。借助于对碱不稳定的保护基的合成α-促黑素及其信息序列（作者的翻译）]。

  摘要：

  Hormone‐Receptor Interactions. Synthesses of α‐Melanotropin and of Informational Sequences thereof with the Aid of Alcali‐Labile Protecting Groups.The aim of this investigation was to prepare α‐melanotropin and partial sequences thereof for biological investigations in as pure a state as possible. Classical synthesis in solution was chosen as the general approach, because it allows for extensive purification and identification of all intermediates, thus warranting the chemical identity of the products (in contrast to the solidphase methods). The scheme of protection was as follows: for the Nα‐amino groups mostly t‐butoxycarbonyl (BOC‐), sometimes benzyloxycarbonyl (Z‐), for the Nϵ‐amino group of lysine‐(11) 2‐(methylsulfonyl)‐ethoxycarbonyl (MSOC‐), and for the carboxylic acid group of C‐terminal glycine‐(10) 2‐(4‐tolyl‐sulfonyl)‐ethoxy (‐OTSE). This provides for facile and mild selective deprotection of either the α‐amino groups by acidolysis or of the ϵ‐amino group (α‐carboxyl group) by β‐elimination in alcali. A slight molar excess of 0.12N HCl in HCOOH proved to be the method of choice for removing BOC‐; MSOC‐ is stable in acid (even for 30 min in liquid HF) and easily removed in a few minutes by 0.05‐‐0.1N Ba(OH)2; ‐OTSE is removed similarly. Condensation of amino‐acid and peptide derivatives (formation of the peptide link) was performed using active esters (‐ONP; ‐OSU), dicyclohexyl‐carbodiimide (DCCI) with or without 1‐hydroxy‐benzotriazole (HOBT), or carboxylic acid azides wherever histidine was the carboxylic component.More than 50 compounds are described. Those characterized by arabic numerals served to prove that α‐MSH contains two message sequences that are able to trigger melanocyte response: one in the central region ‐His‐Phe‐Arg‐Trp‐, the other in the C‐terminal portion ‐Gly‐Lys‐Pro‐Val · NH2 of the molecule [3].

  DOI：

  10.1002/hlca.19750580724

文献信息

• Elimination–addition. Part XVI. Elimination in 2-sulphonylethyl carboxylates: a method for the protection of carboxy-groups in peptide synthesis
  作者：A. W. Miller、C. J. M. Stirling

  DOI：10.1039/j39680002612

  日期：——

  reaction provides the basis of a method for the protection of carboxy-groups during peptide synthesis. The sequence involves formation of 2-toluene-p-sulphonylethyl esters of amino-acids or peptides which are then coupled with N-protected amino-acids to give fully protected peptides. These, on mild treatment with bases, liberate N-protected peptides. 2-Toluene-p-sulphonylethyl esters are stable under

  在弱碱性条件下，可从羧酸的2-磺酰基乙基酯迅速消除羧酸根离子。该反应提供了在肽合成过程中保护羧基的方法的基础。该序列涉及氨基酸或肽的2-甲苯-对-磺酰基乙基酯的形成，然后将其与N-保护的氨基酸偶联以得到完全保护的肽。在用碱温和处理时，它们释放出N-保护的肽。2-甲苯-对-磺酰基乙基酯在用于通过混合碳酸酐，对-硝基苯基酯和二环己基碳二亚胺方法偶联的条件下是稳定的。