3-亚磺基-DL-缬氨酸 | 98462-04-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 缬氨酸类衍生物
• 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: 3-亚磺基-DL-缬氨酸
• 英文名称: 2-amino-3-methyl-3-sulfinobutanoic acid
• CAS: 98462-04-5
• 化学式: C₅H₁₁NO₄S
• 分子量: 181.213
• InChiKey: SVIZNTHNFAOGAB-UHFFFAOYSA-N

物化性质

• 熔点：
  177-179°C (dec.)
• 沸点：
  429.7±55.0 °C(Predicted)
• 密度：
  1.551±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（稍微加热）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  sodium sulbactam 在 sodium hydroxide 作用下， 反应 0.17h， 生成 3-亚磺基-DL-缬氨酸
  参考文献：
  名称：

  Degradation kinetics of sodium sulbactam in aqueous solutions.

  摘要：

  在35°C和0.5的离子强度下，研究了磺苄西钠在各种缓冲溶液中的降解动力学，pH值范围为0.74至9.95。通过离子对反相高效液相色谱法测定磺苄西钠的完整数量和降解产物。降解动力学与磺苄西钠降解为2-氨基-3-甲基-3-亚磺酸丁酸和甲酰乙酸的方案一致，该方案通过5-羧基-6-甲基-6-亚磺酰基-4-氮杂-2-庚烯酸（一种不稳定的中间体）进行。在各种pH值下观察到的降解速率遵循伪一级动力学。pH-速率曲线表明，磺苄西钠在pH值为3.0至7.0的范围内具有最大的稳定性，并且在所研究的整个pH范围内，磺苄西钠比克拉维酸钾稳定得多。

  DOI：

  10.1248/cpb.33.2461

文献信息

• Alkaline degradation of sulbactam.
  作者：JUN HAGINAKA、JUNKO WAKAI、HIROYUKI YASUDA、TOYOZO UNO、TERUMICHI NAKAGAWA

  DOI：10.1248/cpb.33.2035

  日期：——

  Alkaline degradation of sodium sulbactam in methanol and in an aqueous solution has been investigated. The degradation in alkaline methanol produced methyl 5-carboxy-6-methyl-6-sulfino-4-aza-2-heptenoate (II) which showed an ultraviolet (UV) absorption maximum at 279 nm. The UV absorption almost disappeared when the solution was acidified with methanolic HCl solution, and reappeared on subsequent realkalization, suggesting interconversion between II and its protonated form. The degradation in aqueous alkaline solutions yielded 5-carboxy-6-methyl-6-sulfino-4-aza-2-heptenoic acid (IV), which showed λmax at 267 nm. IV was further degraded to 2-amino-3-methyl-3-sulfinobutanoic acid and formylacetic acid. The UV absorption of II and IV almost disappeared in aqueous acidic conditions, and reappeared on subsequent realkalization. These changes could be due to the hydrolysis of enamines II and IV to yield methyl formylacetate and formylacetic acid, respectively, in acidic conditions, and to the generation of the corresponding enolate ions on realkalization.

  已经研究了舒巴坦钠在甲醇和水溶液中的碱降解。在碱性甲醇中降解产生 5-羧基-6-甲基-6-亚磺基-4-氮杂-2-庚烯酸甲酯 (II)，其在 279 nm 处显示出最大紫外线 (UV) 吸收。当溶液用盐酸甲醇溶液酸化时，紫外吸收几乎消失，并在随后的再碱化中重新出现，表明 II 与其质子化形式之间发生了相互转化。在碱性水溶液中降解产生 5-羧基-6-甲基-6-亚磺基-4-氮杂-2-庚烯酸 (IV)，其在 267 nm 处显示 λmax。 IV进一步降解为2-氨基-3-甲基-3-亚磺基丁酸和甲酰乙酸。 II 和 IV 的紫外吸收在酸性水溶液条件下几乎消失，并在随后的再碱化中重新出现。这些变化可能是由于烯胺 II 和 IV 在酸性条件下分别水解产生甲酰乙酸甲酯和甲酰乙酸，以及在再碱化时生成相应的烯醇离子。
• Kinetics and Mechanism of the Reactions of Superoxochromium(III) Ion with Biological Thiols
  作者：Joaquin F. Perez-Benito、Conchita Arias

  DOI：10.1021/jp9809336

  日期：1998.7.1

  The kinetics of the oxidation of three biological thiols (L-cysteine, glutathione, and DL-penicillamine) to their sulfinic and sulfonic acid derivatives by CrOO2+ in aqueous perchloric acid and in the presence of 2-propanol have been studied spectrophotometrically with the aid of the initial-rates method. The kinetic order of the oxidant is 2, whereas that of the reductant is not defined. The acidity of the medium has a slight effect on the initial rates (acid catalysis for both L-cysteine and DL-penicillamine and base catalysis for glutathione). An increase of the ionic strength leads to a rise of the initial rate for both L-cysteine and DL-penicillamine, whereas the initial rate for glutathione is insensitive to the ionic strength. The reactions are inhibited by both 2-propanol and dissolved O-2 and catalyzed by Mn2+, whereas Ce3+ has almost no effect on them. At low 2-propanol concentration and in the absence of Mn2+ the initial rate vs temperature plots have a minimum at around 20 degrees C, whereas in the presence of either concentrated 2-propanol or Mn2+ the Arrhenius law is fulfilled. A single mechanism is proposed for the three reactions involving a CrOO2+/thiol complex, CrOOH2+, and CrO2+ as intermediates. The bimolecular rate constants for the reactions of the intermediate CrO2+ with L-cysteine and DL-penicillamine at 25.0 degrees C have been obtained (around 10(3) M-1 s(-1) in both cases). Some kinetic data for the decomposition of CrOO2+ in the absence of thiol are also given.
• HAGINAKA, JUN;WAKAI, JUNKO;YASUDA, HIROYUKI;UNO, TOYOZO;NAKAGAWA, TERUMIC+, CHEM. AND PHARM. BULL., 1985, 33, N 5, 2035-2043
  作者：HAGINAKA, JUN、WAKAI, JUNKO、YASUDA, HIROYUKI、UNO, TOYOZO、NAKAGAWA, TERUMIC+

  DOI：——

  日期：——