N-4-pentenoyl-L-phenylalanine cyanomethyl ester | 201869-53-6

• 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-4-pentenoyl-L-phenylalanine cyanomethyl ester
• 英文别名: N-pentenoyl-L-phenylalanine cyanomethyl ester；cyanomethyl (2S)-2-(pent-4-enoylamino)-3-phenylpropanoate
• CAS: 201869-53-6
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: YBDUQABVYZDHSA-AWEZNQCLSA-N

物化性质

• 熔点：
  57-58 °C
• 沸点：
  508.0±50.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-4-pentenoyl-L-phenylalanine cyanomethyl ester 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 生成
  参考文献：
  名称：

  A New Strategy for the Synthesis of Bisaminoacylated tRNAs

  摘要：

  Tandemly activated tRNAs participate effectively in protein synthesis and exhibit superior chemical and biochemical stability compared to the more commonly used singly aminoacylated tRNAs. While several bisaminoacylated tRNAs have been prepared via the T4 RNA ligase-mediated condensation of bisaminoacylated pdCpAs and abbreviated tRNA transcripts (tRNA-C(OH)), the bisaminoacylated pdCpAs are difficult to prepare when using bulky amino acids. Described herein is a new strategy for preparing bisaminoacylated tRNAs, applicable even for bulky amino acids.

  DOI：

  10.1021/ol201993c
• 作为产物：
  描述：

  4-戊烯酸 在 碳酸氢钠 、 三乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 40.0h， 生成 N-4-pentenoyl-L-phenylalanine cyanomethyl ester
  参考文献：
  名称：

  用于定点振动光谱的蛋白质的高效同位素编辑

  摘要：

  振动光谱包含有关蛋白质结构和动力学的独特信息。然而，该信息通常被频谱拥塞所掩盖，并且站点选择性信息不可用。原则上，感兴趣的位点可以通过同位素位移进行光谱识别，但如今仅对有利的氨基酸或产量低得令人望而却步的蛋白质的位点特异性同位素标记是可能的。在这里，我们提出了一种有效的无细胞表达系统，用于将任何同位素标记的氨基酸定点掺入蛋白质中。我们从 100 mL 无细胞反应提取物中合成了 1.6 mg 绿色荧光蛋白和同位素标记的酪氨酸。我们明确地确定了时间分辨红外吸收光谱指纹区域中酪氨酸的光谱特征。动力学分析证实了光激发和质子转移之间存在一个持续时间为 3 ps 的中间状态。我们的方法将蛋白质的振动光谱提升到更高水平的结构特异性。

  DOI：

  10.1021/jacs.5b12680

文献信息

• Semisynthesis of 3′(2′)-O-(Aminoacyl)-tRNA Derivatives as Ribosomal Substrate
  作者：Zhiyong Cui、Biliang Zhang

  DOI：10.1002/hlca.200790034

  日期：2007.2

  An efficient synthesis of (3′-terminally) 3′(2′)-O-aminoacylated pCpA derivatives is described, which could lead to the production of (aminoacyl)-tRNAs following T4 RNA ligase mediated ligation. The tetrahydrofuranyl (thf) group was used as a permanent protective group for the 2′-OH of the cytidine moiety which can be removed during the purification of the 3′(2′)-O-aminoacylated-pCpA. This approach

  描述了（3'-末端）3'（2'）- O-氨基酰化的pCpA衍生物的有效合成，这可能导致在T4 RNA连接酶介导的连接后产生（氨酰基）-tRNA。四氢呋喃基（thf）基团是胞苷部分2'-OH的永久保护基，可在纯化3'（2'）- O-氨基酰化-pCpA时将其除去。该方法允许（3'-末端）3'（2'）- O-氨基酰化的寡核苷酸的一般合成。完全保护的pCpA 14是通过亚磷酰胺化学合成的，并用NH 3溶液处理以除去2-氰基乙基和苯甲酰基（  15；方案1和2）。2'- Ô -THF保护的PCPA 15被加上α -氨基甲酸氰甲基酯和产物20A - Ç去保护并用AcOH缓冲液纯化，得到3'（2'） - ö -aminoacylated PCPA 21A - c高产。3'（2'）- O-氨基酰化的pCpA与tRNA（-CA）有效连接，得到（氨酰基）-tRNA，它是核糖体的活性底物。
• 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。
• Analogues of Vaccinia Virus DNA Topoisomerase I Modified at the Active Site Tyrosine
  作者：Rong Gao、Yi Zhang、Ambar K. Choudhury、Larisa M. Dedkova、Sidney M. Hecht

  DOI：10.1021/ja044182z

  日期：2005.3.1

  The mechanism of type IB topoisomerase-mediated DNA relaxation was studied by modification of vaccinia topoisomerase I at the active site tyrosine (position 274) with several tyrosine analogues. These analogues had varied steric, electronic, and stereochemical features to permit assessment of those structural elements required to support topoisomerase function. Eleven tyrosine analogues were successfully incorporated into the active site of vaccinia topoisomerase I. It was found that only tyrosine analogues having the phenolic -OH group in the normal position relative to the protein backbone were active, Modifications that replaced the nucleophilic tyrosine OH (pK(a) approximate to 10.0) group with NH2 (pK(a) 4.6), SH (pK(a) approximate to 7.0), or I groups or that changed the orientation of the nucleophilic OH group essentially eliminated topoisomerase I function. For the active analogues, the electronic effects and H-bonding characteristics of substituents in the meta-position of the aromatic ring may be important in modulating topoisomerase I function. The pH profile for the functional analogues revealed a small shift toward lower pH when compared with wild-type topoisomerase I.
• [EN] METHODS AND COMPOSITIONS FOR AMINOACYL-tRNA SYNTHESIS<br/>[FR] PROCEDES ET COMPOSITIONS PERMETTANT LA SYNTHESE D'AMINOACYLE-ARNT
  申请人：UNIV MASSACHUSETTS

  公开号：WO2003059926A2

  公开（公告）日：2003-07-24

  Methods and compositions are disclosed for the high yield chemical synthesis of 2'(3')-O-aminoacylated oligonucleotides, 2'(3')-O-aminoacylated pCpA derivatives and 2'(3')-aminoacyl-tRNA's. The present invention discloses the use of tetrahydrofuranyl group (THF) as a stable protecting group in the production of aminoacyl-oligonucleotides. THF can also be used in conjunction with a removable protecting group, such as dimethoxytrityl group (DMTr). The mild conditions employed for the removal of the THF group are compatible with the integrity of the aminoacyl linkage as well as tRNA, which makes it possible to utilize the methods of the present invention to form aminoacyl-tRNA's. The present invention discloses an efficient route for synthesizing 2'(3')-aminoacyl-pCpA, which can be used to load any natural amino acid, unnatural amino acid, labeled amino acid, reporter group or derivative thereof onto a tRNA molecule through an aminoacyl linkage.
• A New Strategy for the Synthesis of Bisaminoacylated tRNAs
  作者：Ryan C. Nangreave、Larisa M. Dedkova、Shengxi Chen、Sidney M. Hecht

  DOI：10.1021/ol201993c

  日期：2011.9.16

  Tandemly activated tRNAs participate effectively in protein synthesis and exhibit superior chemical and biochemical stability compared to the more commonly used singly aminoacylated tRNAs. While several bisaminoacylated tRNAs have been prepared via the T4 RNA ligase-mediated condensation of bisaminoacylated pdCpAs and abbreviated tRNA transcripts (tRNA-C(OH)), the bisaminoacylated pdCpAs are difficult to prepare when using bulky amino acids. Described herein is a new strategy for preparing bisaminoacylated tRNAs, applicable even for bulky amino acids.