N-chlorovalylglycine

• 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-chlorovalylglycine
• 英文别名: 2-[[(2S)-2-(chloroamino)-3-methylbutanoyl]amino]acetic acid
• 化学式: C₇H₁₃ClN₂O₃
• 分子量: 208.645
• InChiKey: AOSPFIFFNDAPEW-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-chlorovalylglycine 在 三氧化硫 作用下， 以 various solvent(s) 为溶剂， 生成 L-缬氨酰-甘氨酸
  参考文献：
  名称：

  Rates of Reduction of N-Chlorinated Peptides by Sulfite:  Relevance to Incomplete Dechlorination of Wastewaters

  摘要：

  Biologically induced fragmentation of proteins during wastewater treatment produces peptides, which form long-lasting organic chloramines when the water is disinfected with Cl-2. To protect aquatic wildlife from residual chlorine, including chloramines, wastewaters are often treated with sulfur dioxide or sulfite salts. This strategy incompletely eliminates residual chlorine species. Here we report that dechlorination rate constants of N-chloropeptides are 1-2 order of magnitude smaller than those for NH2Cl and some aliphatic organic chloramines. Slow rates explain the prevalence of N-chloropeptides in dechlorinated wastewaters after faster reacting chlorine species have been eliminated. Dechlorination is subject to general acid catalysis. For N-chlorinated leucylalanine, the rate law above pH 6 in phosphate buffer at 25 degrees C and I approximate to 0.1 M is as follows: rate = (9.92 +/- 0.41 x 10(3)[H2PO4-] + 5.70 +/- 0.52 x 10(8)[H3O+] + 5.3 +/- 0.2)[SO32-][Cl-Leu-Ala] (concentrations in M, time in s). Rate constants for other peptides appear to be of similar magnitude; variations in the acid-catalyzed terms among different hydrophobic peptides correlate with solvation energies of side chains. The kinetic data suggest that reducing N-chloropeptides in wastewaters by 75% or more will require reaction times generally >0.5 h at environmentally acceptable S-IV doses and pH values.

  DOI：

  10.1021/es9707365
• 作为产物：
  描述：

  L-缬氨酰-甘氨酸 在 sodium hypochlorite 作用下， 以 various solvent(s) 为溶剂， 反应 0.17h， 生成 N-chlorovalylglycine
  参考文献：
  名称：

  Rates of Reduction of N-Chlorinated Peptides by Sulfite:  Relevance to Incomplete Dechlorination of Wastewaters

  摘要：

  Biologically induced fragmentation of proteins during wastewater treatment produces peptides, which form long-lasting organic chloramines when the water is disinfected with Cl-2. To protect aquatic wildlife from residual chlorine, including chloramines, wastewaters are often treated with sulfur dioxide or sulfite salts. This strategy incompletely eliminates residual chlorine species. Here we report that dechlorination rate constants of N-chloropeptides are 1-2 order of magnitude smaller than those for NH2Cl and some aliphatic organic chloramines. Slow rates explain the prevalence of N-chloropeptides in dechlorinated wastewaters after faster reacting chlorine species have been eliminated. Dechlorination is subject to general acid catalysis. For N-chlorinated leucylalanine, the rate law above pH 6 in phosphate buffer at 25 degrees C and I approximate to 0.1 M is as follows: rate = (9.92 +/- 0.41 x 10(3)[H2PO4-] + 5.70 +/- 0.52 x 10(8)[H3O+] + 5.3 +/- 0.2)[SO32-][Cl-Leu-Ala] (concentrations in M, time in s). Rate constants for other peptides appear to be of similar magnitude; variations in the acid-catalyzed terms among different hydrophobic peptides correlate with solvation energies of side chains. The kinetic data suggest that reducing N-chloropeptides in wastewaters by 75% or more will require reaction times generally >0.5 h at environmentally acceptable S-IV doses and pH values.

  DOI：

  10.1021/es9707365

文献信息

• Rates of Reduction of N-Chlorinated Peptides by Sulfite:  Relevance to Incomplete Dechlorination of Wastewaters
  作者：James S. Jensen、George R. Helz

  DOI：10.1021/es9707365

  日期：1998.2.1

  Biologically induced fragmentation of proteins during wastewater treatment produces peptides, which form long-lasting organic chloramines when the water is disinfected with Cl-2. To protect aquatic wildlife from residual chlorine, including chloramines, wastewaters are often treated with sulfur dioxide or sulfite salts. This strategy incompletely eliminates residual chlorine species. Here we report that dechlorination rate constants of N-chloropeptides are 1-2 order of magnitude smaller than those for NH2Cl and some aliphatic organic chloramines. Slow rates explain the prevalence of N-chloropeptides in dechlorinated wastewaters after faster reacting chlorine species have been eliminated. Dechlorination is subject to general acid catalysis. For N-chlorinated leucylalanine, the rate law above pH 6 in phosphate buffer at 25 degrees C and I approximate to 0.1 M is as follows: rate = (9.92 +/- 0.41 x 10(3)[H2PO4-] + 5.70 +/- 0.52 x 10(8)[H3O+] + 5.3 +/- 0.2)[SO32-][Cl-Leu-Ala] (concentrations in M, time in s). Rate constants for other peptides appear to be of similar magnitude; variations in the acid-catalyzed terms among different hydrophobic peptides correlate with solvation energies of side chains. The kinetic data suggest that reducing N-chloropeptides in wastewaters by 75% or more will require reaction times generally >0.5 h at environmentally acceptable S-IV doses and pH values.