AcAla-NH2 | 64397-30-4

• 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: AcAla-NH2
• 英文别名: 2-Acetamidopropanamide
• CAS: 64397-30-4；15962-47-7
• 化学式: C₅H₁₀N₂O₂
• mdl: MFCD00136567
• 分子量: 130.147
• InChiKey: DVOVBGJJSFSOPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 储存条件：
  存储于0-5°C环境中

反应信息

• 作为反应物：
  描述：

  AcAla-NH2 、 methyl 2-chloro-3-methyl-6-phenylfuro[3,2-b]pyrazine-7-carboxylate 在 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以73%的产率得到methyl 2-(2-acetamidopropanamido)-3-methyl-6-phenylfuro[3,2-b]pyrazine-7-carboxylate
  参考文献：
  名称：

  Synthesis of functionalized furopyrazines as restricted dipeptidomimetics

  摘要：

  Herein, an efficient synthetic approach to a furopyrazine scaffold with four points of diversity, starting from 2(1H)-pyrazinones, with dipeptomimetic properties, is presented. R-groups corresponding to amino acid side chains were introduced during the 2(1H)-pyrazinone and subsequent furopyrazine formation. The furopyrazine scaffold was further functionalized with an amino- and a carboxy-terminus resulting in a conformationally restricted dipeptidomimetic scaffold. The carboxy-terminus was introduced via a chemoselective vinylation of the 7-position followed by oxidative cleavage, while the amino-terminus was obtained via Buchwald-Hartwig amidation of the 2-position of the scaffold. The versatility of the synthetic method was demonstrated by the synthesis of a small library of diversely substituted furopyrazines having various amino acid side chains on the four points of diversity. Evaluation with an X-ray structure of the scaffold and computational analysis supports the exploitation of the furopyrazine scaffold as a restricted dipeptide mimic, which can mimic the two central residues of a beta-turn. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.022
• 作为产物：
  描述：

  丙酮酸乙酯 在 氨 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以80%的产率得到AcAla-NH2
  参考文献：
  名称：

  Direct, facile synthesis of N-acyl-α-amino amides from α-keto esters and ammonia

  摘要：

  N-酰基-α-氨基酰胺的制备无需色谱纯化，只需在甲醇氨中加热相应的α-酮酯即可。

  DOI：

  10.1039/b808302a

文献信息

• pH-Dependent peptide bond formation by the selective coupling of α-amino acids in water
  作者：Long-Fei Wu、Ziwei Liu、John D. Sutherland

  DOI：10.1039/d0cc06042a

  日期：——

  A novel mechanism enabling selective peptide elongation by coupling α-amino acids over other potentially competing prebiotic amines under acidic aqueous condition is suggested. It proceeds via the generation of a carboxylic acid anhydride intermediate with subsequent intramolecular formation of the amide bond.

  提出了一种新的机制，该机制通过在酸性水溶液条件下将α-氨基酸偶联到其他可能竞争的益生元胺上来实现选择性的肽延长。它通过生成羧酸酐中间体进行，随后在分子内形成酰胺键。
• Eine neue Darstellungsweise von α-N-Formylaminonitrilen, α-N-Formylaminosäureamiden und α- sowie β-Aminosäuren1)
  作者：Friedrich Becke、Peter Päβler

  DOI：10.1002/jlac.19707350106

  日期：——

  Aus Cyanhydrinen 1 von Aldehyden und Ketonen erhält man mit Ameisensäure und Formamid α-N-Formylaminonitrile 2 und α-N-Formylaminosäureamide 3, die sich durch Verseifung in α-Aminosäuren überführen lassen. Außerdem wird gezeigt, daβ-Hydroxynitrile sowie Acrylnitril mit Ameisensäure bei ca. 200° in Polyamide übergehen, die zu β-Aminosäuren verseift werden können.

  从醛和酮，甲酸和甲酰胺给予α-氰醇1 ñ -formylaminonitriles 2和α- Ñ -formylamino酰胺3，其可通过皂化被转换成α氨基酸。还显示出β-羟基腈和丙烯腈在约200°的温度下被甲酸转化为聚酰胺，可以将其皂化为β-氨基酸。
• A model for N-to-C direction in prebiotic peptide synthesis
  作者：Li Zhang、Min Zhang、Xiaofan Guo、Dingwei Gan、Yong Ye、Yufen Zhao、Jianxi Ying

  DOI：10.1039/d3cc06101a

  日期：——

  Drawing inspiration from the initiating amino acid modification in biosynthetic peptides, we have successfully demonstrated a biomimetic mechanism for N-to-C terminal extension in prebiotic peptide synthesis. This achievement was accomplished by using acetylated amino acid amides as the N-terminal substrate for peptide synthesis and amino acid amides as the C-terminal extension, with the reaction carried

  受生物合成肽中起始氨基酸修饰的启发，我们成功证明了益生元肽合成中 N 至 C 末端延伸的仿生机制。这一成果是通过使用乙酰化氨基酸酰胺作为肽合成的N端底物，以氨基酸酰胺作为C端延伸，反应在80℃下以干湿循环进行，不需要任何活化剂。这为益生元肽的形成提供了一条合理的途径。
• PASCAL, ROBERT;ROUSSET, ALAIN;COMMEYRAS, AUGUSTE, NEW J. CHEM., 13,(1989) N, C. 205-214
  作者：PASCAL, ROBERT、ROUSSET, ALAIN、COMMEYRAS, AUGUSTE

  DOI：——

  日期：——
• Synthesis of functionalized furopyrazines as restricted dipeptidomimetics
  作者：Stijn Claerhout、Sweta Sharma、Christian Sköld、Claudia Cavaluzzo、Anja Sandström、Mats Larhed、Meganathan Thirumal、Virinder S. Parmar、Erik V. Van der Eycken

  DOI：10.1016/j.tet.2012.02.022

  日期：2012.4

  Herein, an efficient synthetic approach to a furopyrazine scaffold with four points of diversity, starting from 2(1H)-pyrazinones, with dipeptomimetic properties, is presented. R-groups corresponding to amino acid side chains were introduced during the 2(1H)-pyrazinone and subsequent furopyrazine formation. The furopyrazine scaffold was further functionalized with an amino- and a carboxy-terminus resulting in a conformationally restricted dipeptidomimetic scaffold. The carboxy-terminus was introduced via a chemoselective vinylation of the 7-position followed by oxidative cleavage, while the amino-terminus was obtained via Buchwald-Hartwig amidation of the 2-position of the scaffold. The versatility of the synthetic method was demonstrated by the synthesis of a small library of diversely substituted furopyrazines having various amino acid side chains on the four points of diversity. Evaluation with an X-ray structure of the scaffold and computational analysis supports the exploitation of the furopyrazine scaffold as a restricted dipeptide mimic, which can mimic the two central residues of a beta-turn. (C) 2012 Elsevier Ltd. All rights reserved.