N-pyridoxylidene-L-cysteine | 13933-88-5

• 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
• 英文名称: N-pyridoxylidene-L-cysteine
• CAS: 13933-88-5
• 化学式: C₁₁H₁₄N₂O₄S
• 分子量: 270.309
• InChiKey: HWZHCIZPAUALLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  103.01
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-pyridoxylidene-L-cysteine 以 乙醇 、 水 为溶剂， 生成 2-[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Specific features of the reaction of l-cysteine with pyridoxal and N-pyridoxylidene-β-alanine

  摘要：

  The mechanisms of condensation of l-cysteine, l-methionine, and l-serine with pyridoxal and of transaldimination of N-pyridoxylidene-beta-alanine with l-cysteine were studied by the kinetic method. Unlike methionine and serine, the condensation of cysteine with pyridoxal and transaldimination with Npyridoxylidene-beta-alanine involves intermediate formation of stable product having a thiazolidine ring. Its structure was determined by elemental analysis, UV, and IR spectroscopy, and quantum-chemical calculations. The thiazolidine fragment in the pyridoxal condensation product with l-cysteine is turned through an angle of similar to 90A degrees with respect to the pyridine ring plane due to mutual repulsion of the negatively charged oxygen atom in the ortho position of the pyridine ring and sulfur and nitrogen atoms in the thiazolidine ring.

  DOI：

  10.1134/s1070363212070146
• 作为产物：
  描述：

  L-半胱氨酸 、 吡哆醛盐酸盐 以 乙醇 、 水 为溶剂， 生成 N-pyridoxylidene-L-cysteine
  参考文献：
  名称：

  Specific features of the reaction of l-cysteine with pyridoxal and N-pyridoxylidene-β-alanine

  摘要：

  The mechanisms of condensation of l-cysteine, l-methionine, and l-serine with pyridoxal and of transaldimination of N-pyridoxylidene-beta-alanine with l-cysteine were studied by the kinetic method. Unlike methionine and serine, the condensation of cysteine with pyridoxal and transaldimination with Npyridoxylidene-beta-alanine involves intermediate formation of stable product having a thiazolidine ring. Its structure was determined by elemental analysis, UV, and IR spectroscopy, and quantum-chemical calculations. The thiazolidine fragment in the pyridoxal condensation product with l-cysteine is turned through an angle of similar to 90A degrees with respect to the pyridine ring plane due to mutual repulsion of the negatively charged oxygen atom in the ortho position of the pyridine ring and sulfur and nitrogen atoms in the thiazolidine ring.

  DOI：

  10.1134/s1070363212070146