(2S)-2-acetamido-N-[(1S)-1-[(4S)-4-methyl-5-oxo-4H-1,3-oxazol-2-yl]ethyl]propanamide | 157596-60-6

• 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: (2S)-2-acetamido-N-[(1S)-1-[(4S)-4-methyl-5-oxo-4H-1,3-oxazol-2-yl]ethyl]propanamide
• CAS: 157596-60-6
• 化学式: C₁₁H₁₇N₃O₄
• 分子量: 255.274
• InChiKey: FHOBCSCTNVOEHY-ACZMJKKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-acetamido-N-[(1S)-1-[(4S)-4-methyl-5-oxo-4H-1,3-oxazol-2-yl]ethyl]propanamide 在 三乙胺 作用下， 反应 0.08h， 生成 N-[(S)-2-((2S,5S)-2,5-Dimethyl-3,6-dioxo-piperazin-1-yl)-1-methyl-2-oxo-ethyl]-acetamide
  参考文献：
  名称：

  Activation of the Carboxy Terminus of a Peptide for Carboxy-Terminal Sequencing

  摘要：

  Previously, we reported [Anal. Biochem. 1992, 206, 344-352] a new method of sequencing proteins from the carboxy terminus (C-terminus). The carboxyl group at the C-terminus is activated and derivatized into a thiohydantoin (TH). We reported that, by alkylating the TH formed at the C-terminus, the TH is converted into a readily displaced leaving group. Reaction with {NCS}(-) under acidic conditions cleaves the alkylated thiohydantoin (ATH) and derivatizes the freshly exposed C-terminus into a new proteinyl-TH. The efficiency of the initial activation of the carboxy group at the C-terminus is critical to the initial yield of the first ATH residue. In order to directly observe the intermediates that form during activation of the C-terminus, a model tripeptide, acetylalanine-alanine-alanine-OH (Ac-Ala-Ala-Ala-OH) was subjected to the reagents used to form the peptidyl-TH, Ac-Ala-Ala-Ala-TH. The reaction was monitored by nuclear magnetic resonance spectroscopy. An oxazolone was observed to form immediately at the C-terminus during the reaction with diphenyl chlorophosphate (DPCP), tetraphenyl pyrophosphate (TPPP), or tetramethylchlorouronium chloride (TMU-Cl). The oxazolone was observed to react with an excess of the carboxy group-activating reagents while under basic conditions. Diketopiperazine formation at the C-terminus was also observed. These side reactions prevent or retard the reaction of (NCS)- to form a peptidyl-TH and correlate with a reduced initial yield observed during automated C-terminal protein sequencing. The carboxylic acid-reactive reagents react with the side-chain carboxylic acid groups of aspartic and glutamic acid residues as well as the C-terminus. We found that the sidechain carboxylic acid groups in a protein could be selectively amidated in the presence of the proteinyl-oxazolone at the C-terminus.

  DOI：

  10.1021/jo00113a042
• 作为产物：
  描述：

  N-乙酰基-L-丙氨酰-L-丙氨酰-L-丙氨酸 在 N,N-二异丙基乙胺 、 氯磷酸二苯酯 作用下， 以 氘代乙腈 为溶剂， 生成 (2S)-2-acetamido-N-[(1S)-1-[(4S)-4-methyl-5-oxo-4H-1,3-oxazol-2-yl]ethyl]propanamide
  参考文献：
  名称：

  Activation of the Carboxy Terminus of a Peptide for Carboxy-Terminal Sequencing

  摘要：

  Previously, we reported [Anal. Biochem. 1992, 206, 344-352] a new method of sequencing proteins from the carboxy terminus (C-terminus). The carboxyl group at the C-terminus is activated and derivatized into a thiohydantoin (TH). We reported that, by alkylating the TH formed at the C-terminus, the TH is converted into a readily displaced leaving group. Reaction with {NCS}(-) under acidic conditions cleaves the alkylated thiohydantoin (ATH) and derivatizes the freshly exposed C-terminus into a new proteinyl-TH. The efficiency of the initial activation of the carboxy group at the C-terminus is critical to the initial yield of the first ATH residue. In order to directly observe the intermediates that form during activation of the C-terminus, a model tripeptide, acetylalanine-alanine-alanine-OH (Ac-Ala-Ala-Ala-OH) was subjected to the reagents used to form the peptidyl-TH, Ac-Ala-Ala-Ala-TH. The reaction was monitored by nuclear magnetic resonance spectroscopy. An oxazolone was observed to form immediately at the C-terminus during the reaction with diphenyl chlorophosphate (DPCP), tetraphenyl pyrophosphate (TPPP), or tetramethylchlorouronium chloride (TMU-Cl). The oxazolone was observed to react with an excess of the carboxy group-activating reagents while under basic conditions. Diketopiperazine formation at the C-terminus was also observed. These side reactions prevent or retard the reaction of (NCS)- to form a peptidyl-TH and correlate with a reduced initial yield observed during automated C-terminal protein sequencing. The carboxylic acid-reactive reagents react with the side-chain carboxylic acid groups of aspartic and glutamic acid residues as well as the C-terminus. We found that the sidechain carboxylic acid groups in a protein could be selectively amidated in the presence of the proteinyl-oxazolone at the C-terminus.

  DOI：

  10.1021/jo00113a042

文献信息

• 5(4H)-Oxazolinones as acyl donors in papain-catalyzed peptide fragment condensations
  作者：Byung Keun Hwang、Qu-Ming Gu、Charles J. Sih

  DOI：10.1016/0040-4039(94)85208-1

  日期：1994.4

  Papain, a thiol protease was shown to utilize 5(4H)-oxazolinones of peptides as acyl donors in peptide segment condensations. The effectiveness of this methodology is illustrated by the successful coupling of oxidized insulin B chain (30 residues) to angiotensin III (7 residues) in 59% yield.

  木瓜蛋白酶，一种硫醇蛋白酶，在肽段缩合中显示出利用5（4H）-恶唑啉酮作为酰基供体。该方法的有效性通过氧化胰岛素B链（30个残基）与血管紧张素III（7个残基）的成功偶联以59％的产率得以说明。
• Activation of the Carboxy Terminus of a Peptide for Carboxy-Terminal Sequencing
  作者：Victoria L. Boyd、MeriLisa Bozzini、Piotr J. Guga、Robert J. DeFranco、Pau-Miau Yuan、G. Marc Loudon、Duy Nguyen

  DOI：10.1021/jo00113a042

  日期：1995.4

  Previously, we reported [Anal. Biochem. 1992, 206, 344-352] a new method of sequencing proteins from the carboxy terminus (C-terminus). The carboxyl group at the C-terminus is activated and derivatized into a thiohydantoin (TH). We reported that, by alkylating the TH formed at the C-terminus, the TH is converted into a readily displaced leaving group. Reaction with NCS}(-) under acidic conditions cleaves the alkylated thiohydantoin (ATH) and derivatizes the freshly exposed C-terminus into a new proteinyl-TH. The efficiency of the initial activation of the carboxy group at the C-terminus is critical to the initial yield of the first ATH residue. In order to directly observe the intermediates that form during activation of the C-terminus, a model tripeptide, acetylalanine-alanine-alanine-OH (Ac-Ala-Ala-Ala-OH) was subjected to the reagents used to form the peptidyl-TH, Ac-Ala-Ala-Ala-TH. The reaction was monitored by nuclear magnetic resonance spectroscopy. An oxazolone was observed to form immediately at the C-terminus during the reaction with diphenyl chlorophosphate (DPCP), tetraphenyl pyrophosphate (TPPP), or tetramethylchlorouronium chloride (TMU-Cl). The oxazolone was observed to react with an excess of the carboxy group-activating reagents while under basic conditions. Diketopiperazine formation at the C-terminus was also observed. These side reactions prevent or retard the reaction of (NCS)- to form a peptidyl-TH and correlate with a reduced initial yield observed during automated C-terminal protein sequencing. The carboxylic acid-reactive reagents react with the side-chain carboxylic acid groups of aspartic and glutamic acid residues as well as the C-terminus. We found that the sidechain carboxylic acid groups in a protein could be selectively amidated in the presence of the proteinyl-oxazolone at the C-terminus.