(S)-cyanomethyl 2-acetamido-3-phenylpropanoate | 61781-58-6

• 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: (S)-cyanomethyl 2-acetamido-3-phenylpropanoate
• 英文别名: cyanomethyl N-acetyl-L-phenylalaninate；N-acetyl-L-phenylalanine cyanomethyl ester；Acf-OCH2CN；N-Acetyl-L-phenylalanin-cyanmethylester；N-acetylphenylalanin cyanomethylester；cyanomethyl (2S)-2-acetamido-3-phenylpropanoate
• CAS: 61781-58-6
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: PJYOJWIOZSLLTM-LBPRGKRZSA-N

物化性质

• 沸点：
  486.1±35.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  6
• 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：

  (S)-cyanomethyl 2-acetamido-3-phenylpropanoate 在 四丁基醋酸铵 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 (S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl 2-acetamido-3-phenylpropanoate
  参考文献：
  名称：

  N-Terminal Protein Modification Using Simple Aminoacyl Transferase Substrates

  摘要：

  Methods for synthetically manipulating protein structure enable greater flexibility in the study of protein function. Previous characterization of the Escherichia coli aminoacyl tRNA transferase (AaT) has shown that it can modify the N-terminus of a protein with an amino acid from a tRNA or a synthetic oligonucleotide donor. Here, we demonstrate that AaT can efficiently use a minimal adenosine substrate, which can be synthesized in one to two steps from readily available starting materials. We have characterized the enzymatic activity of AaT with aminoacyl adenosyl donors and found that reaction products do not inhibit AaT. The use of adenosyl donors removes the substrate limitations imposed by the use of synthetases for tRNA charging and avoids the complex synthesis of an oligonucleotide donor. Thus, our AaT donors increase the potential substrate scope and reaction scale for N-terminal protein modification under conditions that maintain folding.

  DOI：

  10.1021/ja2055098
• 作为产物：
  描述：

  N-乙酰-L-苯丙氨酸 、 溴乙腈 在 caesium carbonate 作用下， 生成 (S)-cyanomethyl 2-acetamido-3-phenylpropanoate
  参考文献：
  名称：

  天然丝氨酸肽组装 - 范围和效用

  摘要：

  这项工作开发了丝氨酸肽组装 (SPA)，它与经典的天然化学连接 (NCL) 形成了互补和对比。无试剂肽键形成方面的进展已应用于丝氨酸（和丝氨酸模型）和一系列 C 端氨基酸，包括不适合 NCL 的庞大残基。SPA 的特别吸引力在于具有零外消旋风险和有利的过程质量强度 (PMI) 的制备级段缩合。机理研究支持先前提出的通过初始酯交换步骤的反应途径。对有利于该途径的因素的理解依赖于硬-软酸碱理论，其中具有最大羰基正电荷的温和活化酯与羟基胺的反应性最强。

  DOI：

  10.1002/ejoc.201601148

文献信息

• The BF₃×OEt₂-Assisted Conversion of Nitriles into Thioamides with Lawesson’s Reagent
  作者：Walther Schmid、Michael Nagl、Claudia Panuschka、Andrea Barta

  DOI：10.1055/s-0028-1083253

  日期：2008.12

  A method for the thiolysis of nitriles by applying Lawesson­’s reagent and facilitated by the addition of boron trifluor­ide-diethyl ether complex is reported. The method opens an easy access to primary thioamides. Aromatic, benzylic, and aliphatic nitriles were converted into the corresponding thioamides in high to quantitative yields (even in unfavorable cases, e.g., ortho-substituted benzonitriles). The reaction was performed in 1,2-dimethoxyethane-tetrahydrofuran or toluene-diethyl ether solvent mixtures at 20-50 ˚C, and exhibited considerable selectivity in the case of multifunctional nitrile substrates, such as cyanomethyl N-acetylphenyl­alaninate, benzoylacetonitrile, 4-cyanobenzamide, 4-acetyl­-benzonitrile, or pent-3-enenitrile.

  报道了一种利用Lawesson试剂进行腈的硫解反应的方法，并通过添加三氟化硼二乙醚复合物来促进反应。该方法为制备一级硫酰胺提供了简便途径。芳香族、苄基和脂肪族腈在高至定量的产率下被转化为相应的硫酰胺（即使在不利情况下，例如邻位取代的苄腈）。反应在1,2-二甲氧基乙烷-四氢呋喃或甲苯-二乙醚溶剂混合物中于20-50℃进行，并对多功能腈底物表现出显著的选择性，如氰甲基N-乙酰苯丙氨酸酯、苯甲酰丙二腈、4-氰基苯甲酰胺、4-乙酰基苯甲腈或戊-3-烯腈。
• Methods of modifying N-termini of a peptide or protein using transferases
  申请人：The Trustees of the University of Pennsylvania

  公开号：US09376700B2

  公开（公告）日：2016-06-28

  The invention includes a selective method of modifying the N-terminus of a protein using an aminoacyl tRNA transferase. In certain embodiments, the method comprises contacting a solution of the protein or peptide with a transferase and a derivative of a molecule, whereby the N-terminus of the protein or peptide is derivatized with the molecule.

  该发明涉及使用氨酰基tRNA转移酶选择性地修改蛋白质的N-末端的方法。在某些实施例中，该方法包括将蛋白质或肽溶液与转移酶和分子衍生物接触，从而使蛋白质或肽的N-末端与该分子衍生物发生衍生化反应。
• Homoserine and Threonine Peptide Assembly
  作者：Michael Pirrung、Nicole Bakas

  DOI：10.1055/s-0036-1589123

  日期：2018.1

  recent success with reagent-less peptide-bond formation through serine-based assembly reactions in organic solvent, their range has been expanded to threonine and homoserine (an aspartic acid precursor) in the N-terminal peptide. Amino acid scope available at the assembly C-terminus includes bulky residues not amenable to classical ligation methods, such as cysteine-based NCL in aqueous media. The method

  借鉴我们最近通过有机溶剂中基于丝氨酸的组装反应形成无试剂肽键的成功，它们的范围已扩展到 N 端肽中的苏氨酸和高丝氨酸（天冬氨酸前体）。组装 C 端可用的氨基酸范围包括不适用于经典连接方法的庞大残基，例如水性介质中基于半胱氨​​酸的 NCL。该方法用于从负鼠中​​组装蛇咬伤毒素中和肽。
• ONE STEP N-TERMINAL TAGGING OF PROTEINS
  申请人：The Trustees of the University of Pennsylvania

  公开号：US20150140605A1

  公开（公告）日：2015-05-21

  The invention includes a selective method of modifying the N-terminus of a protein using an aminoacyl tRNA transferase. In certain embodiments, the method comprises contacting a solution of the protein or peptide with a transferase and a derivative of a molecule, whereby the N-terminus of the protein or peptide is derivatized with the molecule.

  本发明涉及使用氨酰tRNA转移酶选择性地改变蛋白质的N-末端的方法。在某些实施例中，该方法包括将蛋白质或肽的溶液与转移酶和分子的衍生物接触，从而使蛋白质或肽的N-末端与该分子发生衍生化反应。
• PEPTIDE WITH SAFER SECONDARY STRUCTURE, PEPTIDE LIBRARY, AND PRODUCTION METHODS FOR SAME
  申请人：The University of Tokyo

  公开号：EP2647721A1

  公开（公告）日：2013-10-09

  An object of the invention is to provide a peptide having a stabilized secondary structure. The present invention provides a peptide having a secondary structure stabilized by a crosslinked structure and containing at least one combination of a special amino acid of the formula (I): (wherein, (A) represents a single bond or a linking group having, in the main chain thereof, from 1 to 10 atoms; (B) represents a group containing at least one π bond; (C) represents a hydrogen atom or an alkyl group which may be substituted with a substituent; and X represents a group substitutable by a substitution reaction with a sulfanyl group) and an amino acid having, in the side chain thereof, a sulfanyl group; and having the crosslinked structure formed through a thioether bond between the side chain of the special amino acid residue and the sulfanyl group.

  本发明的目的是提供一种具有稳定二级结构的多肽。 本发明提供了一种多肽，它具有通过交联结构稳定的二级结构，并含有至少一种式（I）的特殊氨基酸组合： (其中，(A)代表单键或在其主链中具有 1 至 10 个原子的连接基团；(B)代表至少含有一个 π 键的基团；(C)代表氢原子或可被取代基取代的烷基；X 代表可与硫酰基发生取代反应而被取代的基团）和在其侧链中具有硫酰基的氨基酸；并具有通过特殊氨基酸残基侧链与硫酰基之间的硫醚键而形成的交联结构。