N-乙酰基苏氨酸 | 197302-88-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物
• 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
• 中文名称: N-乙酰基苏氨酸
• 英文名称: N-acetyl-D-threonine
• 英文别名: D-threonine；D-Threonine, N-acetyl-；(2R,3S)-2-acetamido-3-hydroxybutanoic acid
• CAS: 197302-88-8
• 化学式: C₆H₁₁NO₄
• 分子量: 161.158
• InChiKey: PEDXUVCGOLSNLQ-WVZVXSGGSA-N

物化性质

• 沸点：
  443.3±40.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-乙酰基苏氨酸 在 盐酸 作用下， 以 甲醇 为溶剂， 以85%的产率得到D-苏氨酸
  参考文献：
  名称：

  N-酰基氮丙啶-2-酰亚胺向恶唑啉-4-酰亚胺的扩环，恶唑啉-4-酰亚胺是纯β-羟基α-氨基酸的有用前体

  摘要：

  光学活性的N-酰基氮丙啶2​​-酰亚胺或2-羧酸酯在高区域和立体控制下重排为oxazoline-4-酰亚胺或4-羧酸酯。该扩环随后温和的水解允许合成对映体纯的β-羟基α-氨基酸前体。

  DOI：

  10.1016/s0040-4039(97)01630-4
• 作为产物：
  描述：

  (4S,5R)-1-[(4R,5S)-2,5-dimethyl-4,5-dihydro-1,3-oxazole-4-carbonyl]-3,4-dimethyl-5-phenylimidazolidin-2-one 在 lithium hydroxide 、 水 、 双氧水 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 N-乙酰基苏氨酸
  参考文献：
  名称：

  N-酰基氮丙啶-2-酰亚胺向恶唑啉-4-酰亚胺的扩环，恶唑啉-4-酰亚胺是纯β-羟基α-氨基酸的有用前体

  摘要：

  光学活性的N-酰基氮丙啶2​​-酰亚胺或2-羧酸酯在高区域和立体控制下重排为oxazoline-4-酰亚胺或4-羧酸酯。该扩环随后温和的水解允许合成对映体纯的β-羟基α-氨基酸前体。

  DOI：

  10.1016/s0040-4039(97)01630-4

文献信息

• [EN] RESOLUTION OF 3-AMINO ALKYLNITRILES<br/>[FR] DÉDOUBLEMENT DE 3-AMINO ALKYLNITRILES
  申请人：PFIZER PROD INC

  公开号：WO2005040097A1

  公开（公告）日：2005-05-06

  The present invention relates to chiral N-acetyl-alpha-amino acid salts of optically active β-amino alkylnitriles, and also to a process for preparing optically active β-amino alkylnitriles by resolving racemic β-amino alkylnitriles using chiral N-acetyl-alpha-amino acids as resolving agent.

  本发明涉及手性N-乙酰-α-氨基酸盐的光学活性β-氨基烷基腈，以及一种利用手性N-乙酰-α-氨基酸作为分离剂来分离混合物的光学活性β-氨基烷基腈的方法。
• Synthesis of enantiomerically pure trans aziridine-2-carboxylates by diastereoselective Gabriel-cromwell reaction
  作者：Giuliana Cardillo、Luca Gentilucci、Claudia Tomasini、Maria Pilar Visa Castejon-Bordas

  DOI：10.1016/0957-4166(96)00071-7

  日期：1996.3

  Benzyl aziridine-2-carboxylates have been obtained in high yield and selectivity by conjugate addition of ammonia to α,β-unsaturated chiral imides followed by treatment with lithium benzyloxide. A ring-expansion of the aziridine to an oxazoline allowed the determination of the absolute stereochemistry for the newly formed stereogenic centres.

  通过将氨共轭添加到α，β-不饱和手性酰亚胺中，然后用苄氧基锂处理，可以高产率和选择性地获得苄基氮丙啶-2-羧酸苄酯。氮丙啶环扩展成恶唑啉可以确定新形成的立体异构中心的绝对立体化学。
• Resolution of 3-amino alkylnitriles
  申请人：Colberg Juan

  公开号：US20050107453A1

  公开（公告）日：2005-05-19

  The present invention relates to chiral N-acetyl-alpha-amino acid salts of optically active β-amino alkylnitriles, and also to a process for preparing optically active β-amino alkylnitriles by resolving racemic β-amino alkylnitriles using chiral N-acetyl-alpha-amino acids as resolving agent.

  本发明涉及手性N-乙酰-α-氨基酸盐的光学活性β-氨基烷基腈，以及通过使用手性N-乙酰-α-氨基酸作为分离剂，分离外消旋的β-氨基烷基腈制备光学活性β-氨基烷基腈的方法。
• Switching Lysophosphatidylserine G Protein-Coupled Receptor Agonists to Antagonists by Acylation of the Hydrophilic Serine Amine
  作者：Misa Sayama、Akiharu Uwamizu、Masaya Ikubo、Luying Chen、Ge Yan、Yuko Otani、Asuka Inoue、Junken Aoki、Tomohiko Ohwada

  DOI：10.1021/acs.jmedchem.1c00347

  日期：2021.7.22
• Functional Annotation and Three-Dimensional Structure of an Incorrectly Annotated Dihydroorotase from cog3964 in the Amidohydrolase Superfamily
  作者：Argentina Ornelas、Magdalena Korczynska、Sugadev Ragumani、Desigan Kumaran、Tamari Narindoshvili、Brian K. Shoichet、Subramanyam Swaminathan、Frank M. Raushel

  DOI：10.1021/bi301483z

  日期：2013.1.8

  The substrate specificities of two incorrectly annotated enzymes belonging to cog3964 from the amidohydrolase superfamily were determined. This group of enzymes are currently misannotated as either dihydroorotases or adenine deaminases. Atu3266 from Agrobacterium tumefaciens C58 and Oant2987 from Ochrobactrum anthropi ATCC 49188 were found to catalyze the hydrolysis of acetyl-(R)-mandelate and similar esters with values of K-cat/K-m that exceed 10(5) M-1 s(-1). These enzymes do not catalyze the deamination of adenine or the hydrolysis of dihydroorotate. Atu3266 was crystallized and the structure determined to a resolution of 2.62 angstrom. The protein folds as a distorted (beta/alpha)(8) barrel and binds two zincs in the active site. The substrate profile was determined via a combination of computational docking to the three-dimensional structure of Atu3266 and screening of a highly focused library of potential substrates. The initial weak hit was the hydrolysis of N-acetyl-D-serine (k(cat)/K-m = 4 M-1 s(-1)). This was followed by the progressive identification of acetyl-(R)-glycerate (k(cat)/K-m = 4 x 10(2) M-1 s(-1)), acetyl glycolate (k(cat)/K-m = 1.3 x 10(4) M-1 s(-1)), and ultimately acetyl-(R)-mandelate (k(cat)/K-m = 2.8 x 10(2) M-1 s(-1)).