(S)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-2-oxobutanoic acid | 846542-01-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-2-oxobutanoic acid
• 英文别名: (4S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxy-2-oxobutanoic acid
• CAS: 846542-01-6
• 化学式: C₉H₁₄O₆
• 分子量: 218.207
• InChiKey: VBDASDITQZURGQ-FSPLSTOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  草酰乙酸 、 L-甘油醛缩丙酮 在 macrophomate synthase from Macrophoma commelinae 、 magnesium chloride 作用下， 生成 、 (S)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-2-oxobutanoic acid
  参考文献：
  名称：

  The Putative Diels−Alderase Macrophomate Synthase is an Efficient Aldolase

  摘要：

  We find that the putative Diels-Alderase macrophomate synthase (MPS) catalyzes the addition of pyruvate enolate, generated by decarboxylation of oxaloacetate, to a variety of aldehydes. Alkyl, aryl, and heteroaryl aldehydes are accepted as substrates, providing gamma-hydroxy-alpha-ketoacids in 35-95% yield with modest levels of stereochemical control. These aldol products, which are difficult to synthesize by other methods, are formed with efficiency comparable to that of macrophomate. Our results thus provide evidence that a two-step Michael-aldol pathway is a plausible alternative to the postulated [4 + 2] cycloaddition in the MPS-catalyzed addition of pyruvate enolate to 2-pyrones. They are also relevant to understanding the divergent evolution of type II pyruvate aldolases.

  DOI：

  10.1021/ja8017994

文献信息

• The Putative Diels−Alderase Macrophomate Synthase is an Efficient Aldolase
  作者：Jörg M. Serafimov、Dennis Gillingham、Simon Kuster、Donald Hilvert

  DOI：10.1021/ja8017994

  日期：2008.6.1

  We find that the putative Diels-Alderase macrophomate synthase (MPS) catalyzes the addition of pyruvate enolate, generated by decarboxylation of oxaloacetate, to a variety of aldehydes. Alkyl, aryl, and heteroaryl aldehydes are accepted as substrates, providing gamma-hydroxy-alpha-ketoacids in 35-95% yield with modest levels of stereochemical control. These aldol products, which are difficult to synthesize by other methods, are formed with efficiency comparable to that of macrophomate. Our results thus provide evidence that a two-step Michael-aldol pathway is a plausible alternative to the postulated [4 + 2] cycloaddition in the MPS-catalyzed addition of pyruvate enolate to 2-pyrones. They are also relevant to understanding the divergent evolution of type II pyruvate aldolases.