N-Pent-4-enoyl-L-methionine methyl ester | 163926-92-9

• 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: N-Pent-4-enoyl-L-methionine methyl ester
• 英文别名: methyl (2S)-4-methylsulfanyl-2-(pent-4-enoylamino)butanoate
• CAS: 163926-92-9
• 化学式: C₁₁H₁₉NO₃S
• 分子量: 245.343
• InChiKey: VRQYCDTWIYVBOI-VIFPVBQESA-N

物化性质

• 沸点：
  405.5±45.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Pent-4-enoyl-L-methionine methyl ester 在 盐酸 、 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 以89%的产率得到L-蛋氨酸甲酯盐酸盐
  参考文献：
  名称：

  Two New Orthogonal Amine-Protecting Groups that can be Cleaved under Mild or Neutral Conditions

  摘要：

  DOI：

  10.1021/ja00116a047
• 作为产物：
  描述：

  4-戊烯酰氯 在 吡啶 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.83h， 生成 N-Pent-4-enoyl-L-methionine methyl ester
  参考文献：
  名称：

  The Pent-4-enoyl Group: A Novel Amine-Protecting Group That Is Readily Cleaved under Mild Conditions

  摘要：

  Primary and secondary amines are readily protected as N-pent-4-enoyl derivatives, the resulting N-pent-4-enamides being usually highly crystalline. Deprotection is rapidly and efficiently effected under mild conditions by treatment with 3 equiv of iodine in aqueous THF solution. Although an oxidizing medium, these deprotection conditions do not affect oxidizable functionalities including p-methoxybenzyl ethers and alkyl sulfides.

  DOI：

  10.1021/jo00129a036

文献信息

• Misacylated Transfer RNAs Having a Chemically Removable Protecting Group
  作者：Michiel Lodder、Serguei Golovine、Andrei L. Laikhter、Vladimir A. Karginov、Sidney M. Hecht

  DOI：10.1021/jo971692l

  日期：1998.2.1

  The 4-pentenoyl group and a number of derivatives have been studied as protecting groups for N(alpha) of the aminoacyl moiety in misacylated tRNAs. The unsubstituted 4-pentenoyl group itself was found to function as efficiently as any of the derivatives studied. Four different N-(4-pentenoyl)aminoacyl-tRNA(CUA)s were prepared and shown to undergo deprotection readily upon admixture of aqueous iodine;

  已经研究了4-戊烯酰基和许多衍生物作为错误酰基化的tRNA中氨基酰基部分的Nα的保护基。发现未取代的4-戊烯酰基本身与任何研究的衍生物一样有效地起作用。制备了四种不同的N-（4-戊烯酰基）氨基酰基-tRNA（CUA），并显示在与碘水溶液混合后易于进行脱保护。在体外蛋白质生物合成系统中，衍生的错误酰化的tRNA都可作为无义密码子的抑制剂发挥良好的功能。还制备了在侧链羧酸酯上被保护的四个Nα-（4-戊烯酰基）天冬氨酰-tRNA（CUA），作为硝化过的烷基酯。用碘水溶液处理后 通过抑制mRNA中的UAG密码子，错误酰化的抑制性tRNA将天冬氨酸衍生物掺入二氢叶酸还原酶的27位。抑制产量明显好于没有侧链保护时的抑制产量。所得的“笼状蛋白”是无活性的，但是在足以使侧链羧酸酯部分脱保护的条件下，通过辐照恢复了全部催化潜力。
• Synthesis of bisaminoacylated pdCpAs and tandemly activated transfer RNAs
  作者：Maria Duca、David J. Maloney、Michiel Lodder、Bixun Wang、Sidney M. Hecht

  DOI：10.1016/j.bmc.2007.03.088

  日期：2007.7

  Described herein is the preparation of new bisacylated tRNAs and their participation in protein synthesis. It has been reported that Thermus thermophilus phenylalanyl-tRNA synthetase can introduce two phenylalanine moieties onto the 3'-terminal adenosine of its cognate tRNA. It is also possible to prepare bisactivated tRNAs in vitro; these participate in protein synthesis [Wang, B.; Zhou, J.; Lodder, M.; Anderson, R. D.; Hecht, S. M. J Biol. Chem. 2006, 281, 138651. Presently, the chemical strategy used for the synthesis of the key intermediate bisacylated pdCpAs is described. Bis-S-alanyl- and bis-S-methionyl-pdCpAs were prepared initially. Further, S-threonine, S-allo-threonine, S-homoserine, and (S)-(+)-2-amino-3-hydroxy-3-methylbutyric acid were coupled with the dinucleotide to define preparative methods applicable to more complex amino acids bearing additional functionality in the form of an OH group. (c) 2007 Elsevier Ltd. All rights reserved.
• The Pent-4-enoyl Group: A Novel Amine-Protecting Group That Is Readily Cleaved under Mild Conditions
  作者：Robert Madsen、Carmichael Roberts、Bert Fraser-Reid

  DOI：10.1021/jo00129a036

  日期：1995.12

  Primary and secondary amines are readily protected as N-pent-4-enoyl derivatives, the resulting N-pent-4-enamides being usually highly crystalline. Deprotection is rapidly and efficiently effected under mild conditions by treatment with 3 equiv of iodine in aqueous THF solution. Although an oxidizing medium, these deprotection conditions do not affect oxidizable functionalities including p-methoxybenzyl ethers and alkyl sulfides.
• Two New Orthogonal Amine-Protecting Groups that can be Cleaved under Mild or Neutral Conditions
  作者：John S. Debenham、Robert Madsen、Carmichael Roberts、Bert Fraser-Reid

  DOI：10.1021/ja00116a047

  日期：1995.3