2-Iminobutanoic acid | 4250-86-6

• 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: 2-Iminobutanoic acid
• CAS: 4250-86-6
• 化学式: C₄H₇NO₂
• mdl: MFCD19230268
• 分子量: 101.1
• InChiKey: WRBRCYPPGUCRHW-UHFFFAOYSA-N

物化性质

• 沸点：
  172.6±23.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Iminobutanoic acid 、 水 生成 2-oxobutanoate 、 铵
  参考文献：
  名称：

  Arabidopsis and Maize RidA Proteins Preempt Reactive Enamine/Imine Damage to Branched-Chain Amino Acid Biosynthesis in Plastids    

  摘要：

  RidA（反应中间体脱氨酶A）蛋白在各种生物中广泛存在，但它们在真核生物中的功能尚不清楚。已知删除沙门氏菌ridA会导致丝氨酸敏感性，并且沙门氏菌RidA及其它生物体的同源物质可以水解丝氨酸或苏氨酸脱水酶形成的烯胺/亚胺中间体。在沙门氏菌中，丝氨酸衍生的烯胺/亚胺会使支链氨基转移酶失活；RidA可以预防这种损伤。拟南芥和玉米（Zea mays）有一个被预测为质体的RidA同源物。表达任一同源物都可以补充沙门氏菌ridA突变体的丝氨酸敏感性。纯化的蛋白可以水解从丝氨酸或苏氨酸中脱水酶形成的烯胺/亚胺，并保护拟南芥质体支链氨基转移酶BCAT3不受丝氨酸衍生的烯胺/亚胺失活的影响。体外叶绿体导入实验和绿色荧光蛋白融合体内定位显示，拟南芥RidA和脱水酶定位于叶绿体。破坏拟南芥RidA会减缓根的生长并提高支链氨基酸生物合成中间体2-氧丁酸的根和茎水平；丝氨酸处理会加剧这些效应。提供异亮氨酸可以逆转根生长缺陷。这些结果表明，质体RidA蛋白可以通过水解脱水酶产生的丝氨酸衍生烯胺/亚胺产物来预防BCAT3和异亮氨酸生物合成的损伤。

  DOI：

  10.1105/tpc.114.126854
• 作为产物：
  描述：

  dehydrobutyrine 生成 2-Iminobutanoic acid
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Conserved YjgF Protein Family Deaminates Reactive Enamine/Imine Intermediates of Pyridoxal 5′-Phosphate (PLP)-dependent Enzyme Reactions
  作者：Jennifer A. Lambrecht、Jeffrey M. Flynn、Diana M. Downs

  DOI：10.1074/jbc.m111.304477

  日期：2012.1

  The YjgF/YER057c/UK114 family of proteins is conserved in all domains of life, suggesting that the role of these proteins arose early and was maintained throughout evolution. Metabolic consequences of lacking this protein in Salmonella enterica and other organisms have been described, but the biochemical function of YjgF remained unknown. This work provides the first description of a conserved biochemical activity for the YjgF protein family. Our data support the conclusion that YjgF proteins have enamine/imine deaminase activity and accelerate the release of ammonia from reactive enamine/imine intermediates of the pyridoxal 5'-phosphate-dependent threonine dehydratase (IlvA). Results from structure-guided mutagenesis experiments suggest that YjgF lacks a catalytic residue and that it facilitates ammonia release by positioning a critical water molecule in the active site. YjgF is renamed RidA (reactive intermediate/imine deaminase A) to reflect the conserved activity of the protein family described here. This study, combined with previous physiological studies on yjgF mutants, suggests that intermediates of pyridoxal 5'-phosphate-mediated reactions may have metabolic consequences in vivo that were previously unappreciated. The conservation of the RidA/YjgF family suggests that reactive enamine/imine metabolites are of concern to all organisms.