betaine aldehyde hydrate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: betaine aldehyde hydrate
• 英文别名: (2,2-dihydroxy-ethyl)-trimethyl-ammonium；(2,2-Dihydroxy-aethyl)-trimethyl-ammonium；2,2-dihydroxyethyl(trimethyl)azanium
• 化学式: C₅H₁₄NO₂
• 分子量: 120.172
• InChiKey: HEHORKLRCFPRON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氯化胆碱 在 choline oxidase 、 氧气 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.18h， 生成 betaine aldehyde hydrate 、 盐酸甜菜碱
  参考文献：
  名称：

  In vitro visualization of betaine aldehyde synthesis and oxidation using hyperpolarized magnetic resonance spectroscopy

  摘要：

  使用超极化胆碱类似物和13C-NMR，以高时间分辨率实时监测甜菜碱醛代谢。这是首次在超极化磁共振上观察到醛类中间体，为氧化酶/脱氢酶的体外和体内动力学研究开辟了道路。

  DOI：

  10.1039/c3cc42542h

文献信息

• Evidence for a Ferredoxin-Dependent Choline Monooxygenase from Spinach Chloroplast Stroma
  作者：Renaud Brouquisse、Pierre Weigel、David Rhodes、Charles F. Yocum、Andrew D. Hanson

  DOI：10.1104/pp.90.1.322

  日期：1989.5.1

  Chenopods synthesize betaine in the chloroplast via a two-step oxidation of choline: choline → betaine aldehyde → betaine. Our previous experiments with intact chloroplasts, and in vivo18O2 labeling studies, led us to propose that the first step is mediated by a monooxygenase which uses photosynthetically generated reducing power (C Lerma, AD Hanson, D Rhodes [1988] Plant Physiol 88: 695-702). Here, we report the detection of such an activity in vitro. In the presence of O2 and reduced ferredoxin, the stromal fraction from spinach (Spinacia oleracea) chloroplasts converted choline to betaine aldehyde at rates similar to those in intact chloroplasts (20-50 nanomoles per hour per milligram protein). Incorporation of 18O from 18O2 by the in vitro reaction was demonstrated by fast atom bombardment mass spectrometry. Ferredoxin could be reduced either with thylakoids in the light, or with NADPH plus ferredoxin-NADP reductase in darkness; NADPH alone could not substitute for ferredoxin. No choline-oxidizing activity was detected in the stromal fraction of pea (Pisum sativum L.), a species that does not accumulate betaine. The spinach choline-oxidizing enzyme was stimulated by 10 millimolar Mg2+, had a pH optimum close to 8, and was insensitive to carbon monoxide. The specific activity was increased threefold in plants growing in 200 millimolar NaCl. Gel filtration experiments gave a molecular weight of 98 kilodaltons for the choline-oxidizing enzyme, and provided no evidence for other electron carriers which might mediate the reduction of the 98-kilodalton enzyme by ferredoxin.

  藜科植物通过胆碱两步氧化反应在叶绿体中合成甜菜碱：胆碱→甜菜碱醛→甜菜碱。我们之前对完整叶绿体的实验和体内18O2标记研究，使我们提出第一步是由单加氧酶介导的，该酶利用光合作用产生的还原力（C Lerma、AD Hanson、D Rhodes [1988]《植物生理学》88：695-702）。在此，我们报告了在体外检测到这种活性。在O2和还原型铁氧蛋白存在的情况下，菠菜（Spinacia oleracea）叶绿体的基质部分将胆碱转化为甜菜碱醛，其速率与完整叶绿体中的速率相似（每毫克蛋白质每小时20-50毫微摩尔）。通过快速原子轰击质谱法证明了体外反应中18O2掺入18O。铁氧蛋白可以在光线下与类囊体结合，也可以在黑暗中与NADPH和铁氧蛋白-NADP还原酶结合；仅NADPH不能替代铁氧蛋白。在豌豆（Pisum sativum L.）的基质部分中未检测到胆碱氧化活性，该物种不积累甜菜碱。菠菜胆碱氧化酶受10毫摩尔Mg2+刺激，最佳pH值接近8，对一氧化碳不
• In vitro visualization of betaine aldehyde synthesis and oxidation using hyperpolarized magnetic resonance spectroscopy
  作者：Hyla Allouche-Arnon、Ayelet Gamliel、Jacob Sosna、J. Moshe Gomori、Rachel Katz-Brull

  DOI：10.1039/c3cc42542h

  日期：——

  Real-time monitoring of betaine aldehyde metabolism at high temporal resolution was accomplished using a hyperpolarized choline analog and 13C-NMR. This represents the first observation of an aldehyde intermediate on hyperpolarized MR and opens the way for kinetic studies of oxidase/dehydrogenase enzymes in vitro and in vivo.

  使用超极化胆碱类似物和13C-NMR，以高时间分辨率实时监测甜菜碱醛代谢。这是首次在超极化磁共振上观察到醛类中间体，为氧化酶/脱氢酶的体外和体内动力学研究开辟了道路。