(-)-3-氨基-1-羟基-2-吡咯酮 | 111821-58-0

• 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: (-)-3-氨基-1-羟基-2-吡咯酮
• 中文别名: (S)-(-)-3-氨基-1-羟基-2-吡咯烷酮
• 英文名称: (-)-HA 966
• 英文别名: (S)-(-)-HA-966；(3S)-3-amino-1-hydroxypyrrolidin-2-one
• CAS: 111821-58-0
• 化学式: C₄H₈N₂O₂
• 分子量: 116.12
• InChiKey: HCKUBNLZMKAEIN-VKHMYHEASA-N

物化性质

• 熔点：
  166℃
• 沸点：
  259℃
• 密度：
  1.436
• 闪点：
  110℃

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-3-氨基-1-羟基-2-吡咯酮 在 盐酸 作用下， 反应 4.0h， 以71%的产率得到4-N-hydroxy-L-2,4-diaminobutyric acid hydrochloride
  参考文献：
  名称：

  4-N-Hydroxy-L-2,4-diaminobutyric acid. A strong inhibitor of glutamine synthetase

  摘要：

  Analogues of glutamic acid were synthesized and evaluated for their inhibitory activity toward glutamine synthetase (EC 6.3.1.2; GS). The title compound, 4-N-hydroxy-L-2,4-diaminobutyric acid (NH-DABA), showed a potent inhibitory activity against GS from both sheep brain and soybean. The inhibition is competitive with respect to glutamic acid and the Ki values of sheep brain GS and soybean GS for NH-DABA are 0.007 mmol and 0.021 mmol, respectively. The activity of inhibition is comparable to those of L-methionine sulfoximine and 2-amino-4-(hydroxymethyl-phosphinyl)butyric acid (phosphinothricin).

  DOI：

  10.1021/jm00397a037
• 作为产物：
  描述：

  ((S)-1-Hydroxy-2-oxo-pyrrolidin-3-yl)-carbamic acid benzyl ester 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.17h， 以98%的产率得到(-)-3-氨基-1-羟基-2-吡咯酮
  参考文献：
  名称：

  4-N-Hydroxy-L-2,4-diaminobutyric acid. A strong inhibitor of glutamine synthetase

  摘要：

  Analogues of glutamic acid were synthesized and evaluated for their inhibitory activity toward glutamine synthetase (EC 6.3.1.2; GS). The title compound, 4-N-hydroxy-L-2,4-diaminobutyric acid (NH-DABA), showed a potent inhibitory activity against GS from both sheep brain and soybean. The inhibition is competitive with respect to glutamic acid and the Ki values of sheep brain GS and soybean GS for NH-DABA are 0.007 mmol and 0.021 mmol, respectively. The activity of inhibition is comparable to those of L-methionine sulfoximine and 2-amino-4-(hydroxymethyl-phosphinyl)butyric acid (phosphinothricin).

  DOI：

  10.1021/jm00397a037

文献信息

• Resolution and synthesis of the individual enantiomers of the glycine antagonist 3-amino-1-hydroxypyrrolidin-2-one (HA-966)
  作者：Brian J. Williams、Paul D. Leeson、Graeme Hannah、Raymond Baker

  DOI：10.1039/c39890001740

  日期：——

  The individual enantiomers of the glycine antagonist HA-966 (1) have been obtained by resolution via the bis-Boc-L-Phe (Boc = t-butoxycarbonyl) derivatives (2a and 2b) and by synthesis from D- and L-methionine.

  甘氨酸拮抗剂HA-966（1）的单个对映体是通过bis-Boc- L -Phe（Boc =叔丁氧羰基）衍生物（2a和2b）拆分并由D-和L-蛋氨酸合成而获得的。
• WILLIAMS, BRIAN J.;LEESON, PAUL D.;HANNAH, GRAEME;BAKER, RAYMOND, J. CHEM. SOC. CHEM. COMMUN.,(1989) N2, C. 1740-1742
  作者：WILLIAMS, BRIAN J.、LEESON, PAUL D.、HANNAH, GRAEME、BAKER, RAYMOND

  DOI：——

  日期：——
• FUSHIYA, SHINJI;MAEDA, KAZUTOSHI;FUNAYAMA, TOSHIHIKO;NOZOE, SHIGEO, J. MED. CHEM., 31,(1988) N 2, 480-483
  作者：FUSHIYA, SHINJI、MAEDA, KAZUTOSHI、FUNAYAMA, TOSHIHIKO、NOZOE, SHIGEO

  DOI：——

  日期：——
• 4-N-Hydroxy-L-2,4-diaminobutyric acid. A strong inhibitor of glutamine synthetase
  作者：Shinji Fushiya、Kazutoshi Maeda、Toshihiko Funayama、Shigeo Nozoe

  DOI：10.1021/jm00397a037

  日期：1988.2

  Analogues of glutamic acid were synthesized and evaluated for their inhibitory activity toward glutamine synthetase (EC 6.3.1.2; GS). The title compound, 4-N-hydroxy-L-2,4-diaminobutyric acid (NH-DABA), showed a potent inhibitory activity against GS from both sheep brain and soybean. The inhibition is competitive with respect to glutamic acid and the Ki values of sheep brain GS and soybean GS for NH-DABA are 0.007 mmol and 0.021 mmol, respectively. The activity of inhibition is comparable to those of L-methionine sulfoximine and 2-amino-4-(hydroxymethyl-phosphinyl)butyric acid (phosphinothricin).