N-NVOC-L-phenylalanine cyanomethyl ester | 132018-86-1

• 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: N-NVOC-L-phenylalanine cyanomethyl ester
• 英文别名: cyanomethyl (2S)-2-[(4,5-dimethoxy-2-nitrophenyl)methoxycarbonylamino]-3-phenylpropanoate
• CAS: 132018-86-1
• 化学式: C₂₁H₂₁N₃O₈
• 分子量: 443.413
• InChiKey: BYSLKNSYVKWYSB-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-NVOC-L-phenylalanine cyanomethyl ester 、 cytidylyl (3'-> 5') adenosine 5'-monophosphate 在 三乙胺 、 tetrabutylammonium phosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以72%的产率得到
  参考文献：
  名称：

  Facile Synthesis of N-Acyl-aminoacyl-pCpA for Preparation of Mischarged Fully Ribo tRNA

  摘要：

  Chemical synthesis of N-acyl-aminoacyl-pdCpA and its ligation to tRNA(minus) CA is widely used for the preparation of unnatural aminoacyl-tRNA substrates for ribosomal translation. However, the presence of the unnatural deoxyribose can decrease incorporation yield in translation and there is no straightforward method for chemical synthesis of the natural ribo version. Here, we show that pCpA is surprisingly stable to treatment with strong organic bases provided that anhydrous conditions are used. This allowed development of a facile method for chemical aminoacylation of pCpA. Preparative synthesis of pCpA was also simplified by using t-butyl-dithiomethyl protecting group methodology, and a more reliable pCpA postpurification treatment method was developed. Such aminoacyl-pCpA analogues ligated to tRNA(minus) CA transcripts are highly active in a purified translation system, demonstrating utility of our synthetic method.

  DOI：

  10.1021/bc500441b
• 作为产物：
  描述：

  L-苯丙氨酸 在 sodium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 25.0h， 生成 N-NVOC-L-phenylalanine cyanomethyl ester
  参考文献：
  名称：

  转移 RNA 化学氨酰化的通用有效途径

  摘要：

  详述了通过N-保护的α-氨基酸的氰甲基活性酯与pdCpA反应一步高产率制备氨酰基pdCpA。还研究了含有硝基草酰 (NVOC) N 保护氨基酸的氨酰基 pdCpA 衍生物的制备和光脱保护。通过将 NVOC-苯丙氨酰 pdCpA 酶促连接到 tRNA-C OH，然后光解以提供未保护的苯丙氨酰 tRNA，证实了上述制备氨酰 tRNA 的方法的效用。苯丙氨酰 tRNA 被证明在体外蛋白质生物合成系统中是有能力的。这些协议极大地简化了化学错酰化 tRNA 在含有非天然氨基酸的蛋白质合成以及蛋白质生物合成研究中的使用

  DOI：

  10.1021/ja00007a055

文献信息

• Specificity of Translation for <i>N</i>-Alkyl Amino Acids
  作者：Baolin Zhang、Zhongping Tan、Lucas Gartenmann Dickson、Madhavi N. L. Nalam、Virginia W. Cornish、Anthony C. Forster

  DOI：10.1021/ja073487l

  日期：2007.9.1

  We examine the specificity of translation for various primary and secondary amino acid analogues. A synthetase-free, pure, E. coli translation system is used to prevent competing reactions, and three different tRNA adaptor:codon pairs are used to control for tRNA- and codon-specific effects. Surprisingly, N -butyl amino acids fail to incorporate, N -methyl amino acid incorporation efficiencies are dependent on the tRNA adaptor, yet hydroxyPro, Pro, Phe, and Ala incorporate near quantitatively from all adaptors. This suggests that Pro is a privileged N -alkyl amino acid for incorporation by the translation apparatus and establishes that very efficient N -methyl amino acid incorporation is possible if matched with an optimal tRNA adaptor. Results support exploration of Pro analogues and N -methyl amino acids as substrates for engineering ribosomal synthesis of genetically selectable libraries of protease-resistant, N -alkyl peptide ligands.
• [EN] PROTEIN SYNTHESIS USING MODIFIED RIBOSOMES<br/>[FR] SYNTHESE DE PROTEINES REALISEE AU MOYEN DE RIBOSOMES MODIFIES
  申请人：UNIV VIRGINIA

  公开号：WO2004035757A2

  公开（公告）日：2004-04-29

  The present invention is directed to modified ribosomes and methods of using such modified ribosomes to synthesize proteins that contain an unusual amino acid. In particular, the modified ribosomes show an enhanced facility relative to wild type ribosomes for incorporating D-amino acids and other modified amino acids into a protein's primary sequence.
• A general and efficient route for chemical aminoacylation of transfer RNAs
  作者：Stephanie A. Robertson、Jonathan A. Ellman、Peter G. Schultz

  DOI：10.1021/ja00007a055

  日期：1991.3

  The preparation of aminoacyl pdCpA in one step and in high yield by reaction of the cyanomethyl active esters of N-protected α-amino acids with pdCpA is detailed. The preparation and photodeprotection of aminoacyl pdCpA derivatives containing nitroveratryl (NVOC) N-protected amino acids is also studied. The utility of the above methods for preparing aminoacyl tRNA was confirmed by enzymatically ligating

  详述了通过N-保护的α-氨基酸的氰甲基活性酯与pdCpA反应一步高产率制备氨酰基pdCpA。还研究了含有硝基草酰 (NVOC) N 保护氨基酸的氨酰基 pdCpA 衍生物的制备和光脱保护。通过将 NVOC-苯丙氨酰 pdCpA 酶促连接到 tRNA-C OH，然后光解以提供未保护的苯丙氨酰 tRNA，证实了上述制备氨酰 tRNA 的方法的效用。苯丙氨酰 tRNA 被证明在体外蛋白质生物合成系统中是有能力的。这些协议极大地简化了化学错酰化 tRNA 在含有非天然氨基酸的蛋白质合成以及蛋白质生物合成研究中的使用
• Facile Synthesis of <i>N</i>-Acyl-aminoacyl-pCpA for Preparation of Mischarged Fully Ribo tRNA
  作者：Marek Kwiatkowski、Jinfan Wang、Anthony C. Forster

  DOI：10.1021/bc500441b

  日期：2014.11.19

  Chemical synthesis of N-acyl-aminoacyl-pdCpA and its ligation to tRNA(minus) CA is widely used for the preparation of unnatural aminoacyl-tRNA substrates for ribosomal translation. However, the presence of the unnatural deoxyribose can decrease incorporation yield in translation and there is no straightforward method for chemical synthesis of the natural ribo version. Here, we show that pCpA is surprisingly stable to treatment with strong organic bases provided that anhydrous conditions are used. This allowed development of a facile method for chemical aminoacylation of pCpA. Preparative synthesis of pCpA was also simplified by using t-butyl-dithiomethyl protecting group methodology, and a more reliable pCpA postpurification treatment method was developed. Such aminoacyl-pCpA analogues ligated to tRNA(minus) CA transcripts are highly active in a purified translation system, demonstrating utility of our synthetic method.