β-acetylamino-L-alanine | 20584-70-7

• 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: β-acetylamino-L-alanine
• 英文别名: L-3-acetyl-amino-2-amino-propionic acid；β-Acetyl-α-β-diaminopropionsaeure；β-Acetyl-L-2,3-diaminopropionsaeure；(S)-3-acetylamino-2-amino-propionic acid；(S)-3-Acetylamino-2-amino-propionsaeure；(2S)-2-amino-3-acetamidopropanoic acid；(2S)-3-acetamido-2-aminopropanoic acid
• CAS: 20584-70-7
• 化学式: C₅H₁₀N₂O₃
• 分子量: 146.146
• InChiKey: YSPAKPPINKSOKX-BYPYZUCNSA-N

物化性质

• 熔点：
  175-178 °C
• 沸点：
  423.3±40.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  β-acetylamino-L-alanine 在 对甲苯磺酸 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 19.0h， 生成 α-R-mandeloyl-β-acetylamino-L-alanine benzhydryl ester
  参考文献：
  名称：

  手性异恶唑烷-5-酮的合成及其在β-氨基丙氨酸和β-（N-羟氨基）丙氨酸合成中的应用

  摘要：

  在本文中，我们报道了高产的异恶唑烷丁5-酮的合成及其在合成β-氨基丙氨酸和β-（N-羟基氨基）-丙氨酸中的用途。

  DOI：

  10.1016/s0040-4020(01)90416-8
• 作为产物：
  描述：

  Nα-CBz-β-acetylamino-L-alanine 在 10% palladium on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 β-acetylamino-L-alanine
  参考文献：
  名称：

  On-Bead Screening of a Combinatorial Fumaric Acid Derived Peptide Library Yields Antiplasmodial Cysteine Protease Inhibitors with Unusual Peptide Sequences

  摘要：

  A new class of cysteine protease inhibitors based oil fumaric acid derived oligopeptides was successfully identified from a high-throughput screening of a solid-phase bound combinatorial library. As target enzymes falcipain and rhodesain were used, which play important roles in the life cycles of the parasites which cause malaria (Plasmodium falciparum) and African sleeping sickness (Trypanosoma brucei rhodesiense). The best inhibitors with unusual amino acid sequences not reported before for this type of enzyme were also fully analyzed in detail in solution. K-i values in the lower micromolar and even nanomolar region were found. Some inhibitors are even active against plasmodia and show good selectivity relative to other enzymes. Also the mechanism of action was studied and could be shown to be irreversible inhibition.

  DOI：

  10.1021/jm900629w

文献信息

• Utilization of Alternate Substrates by the First Three Modules of the Epothilone Synthetase Assembly Line
  作者：Tanya L. Schneider、Christopher T. Walsh、Sarah E. O'Connor

  DOI：10.1021/ja0274498

  日期：2002.9.1

  the enzymatic construction of alternate heterocyclic structures and the subsequent elongation of these products by the third enzyme of the pathway, EpoC. The epothilone biosynthetic machinery can utilize serine to install an oxazole in place of a thiazole in the epothilone structure and will tolerate functionalized donor groups from the EpoA-ACP domain to produce epothilone fragments modified at the C21

  埃坡霉素是由粘细菌种 Sorangium cellulosum 产生的大环内酯天然产物家族，目前作为抗肿瘤剂具有临床意义。埃坡霉素结构的检查表明杂合聚酮化合物/非核糖体肽生物合成起源，最近埃坡霉素生物合成基因簇的测序证实了这一提议。在这里，我们用生物合成途径的前两种酶 EpoA 和 EpoB 检测了非天然底物，以研究交替杂环结构的酶促构建以及该途径的第三种酶 EpoC 对这些产物的后续延伸。埃坡霉素生物合成机制可以利用丝氨酸在埃坡霉素结构中安装恶唑代替噻唑，并且将耐受来自 EpoA-ACP 结构域的功能化供体基团以产生在 C21 位置修饰的埃坡霉素片段。这些对埃坡霉素生物合成簇的早期酶的研究表明，组合生物合成可能是生产多种埃坡霉素类似物的可行手段，这些类似物将多样性整合到杂环起始单元中。
• Birnbaum et al., Journal of Biological Chemistry, 1952, vol. 198, p. 335,337,341
  作者：Birnbaum et al.

  DOI：——

  日期：——
• SCHOLTZ, JOHN M.;BARTLETT, PAUL A., BIOORG. CHEM., 17,(1989) N, C. 422-433
  作者：SCHOLTZ, JOHN M.、BARTLETT, PAUL A.

  DOI：——

  日期：——
• Synthesis of chiral isoxazolidin-5-ones and their applications to the synthesis of β-amino-alanines and β-(N-hydroxyamino)-alanines
  作者：Jack E. Baldwin、Robert M. Adlington、Lisa C. Mellor

  DOI：10.1016/s0040-4020(01)90416-8

  日期：1994.4

  Herein we report a high-yielding synthesis of isoxazolidin-5-ones and their use to synthesise both β-amino-alanines and β-(N-hydroxyamino)-alanines.

  在本文中，我们报道了高产的异恶唑烷丁5-酮的合成及其在合成β-氨基丙氨酸和β-（N-羟基氨基）-丙氨酸中的用途。
• On-Bead Screening of a Combinatorial Fumaric Acid Derived Peptide Library Yields Antiplasmodial Cysteine Protease Inhibitors with Unusual Peptide Sequences
  作者：Uwe Machon、Christian Büchold、Martin Stempka、Tanja Schirmeister、Christoph Gelhaus、Matthias Leippe、Jiri Gut、Philip J. Rosenthal、Caroline Kisker、Matthias Leyh、Carsten Schmuck

  DOI：10.1021/jm900629w

  日期：2009.9.24

  A new class of cysteine protease inhibitors based oil fumaric acid derived oligopeptides was successfully identified from a high-throughput screening of a solid-phase bound combinatorial library. As target enzymes falcipain and rhodesain were used, which play important roles in the life cycles of the parasites which cause malaria (Plasmodium falciparum) and African sleeping sickness (Trypanosoma brucei rhodesiense). The best inhibitors with unusual amino acid sequences not reported before for this type of enzyme were also fully analyzed in detail in solution. K-i values in the lower micromolar and even nanomolar region were found. Some inhibitors are even active against plasmodia and show good selectivity relative to other enzymes. Also the mechanism of action was studied and could be shown to be irreversible inhibition.