N-{5-[(tert-Butoxycarbonyl)amino]pentyl}glycine | 630095-93-1

• 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-{5-[(tert-Butoxycarbonyl)amino]pentyl}glycine
• 英文别名: 2-[5-[(2-methylpropan-2-yl)oxycarbonylamino]pentylamino]acetic acid
• CAS: 630095-93-1
• 化学式: C₁₂H₂₄N₂O₄
• 分子量: 260.334
• InChiKey: RITREHUHOOKUBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-{5-[(tert-Butoxycarbonyl)amino]pentyl}glycine 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 N-(5-氨基戊基)甘氨酸
  参考文献：
  名称：

  Metabolization of the Advanced Glycation End ProductN-ε-Carboxymethyllysine (CML) by Different ProbioticE. coliStrains

  摘要：

  N-epsilon-Carboxymethyllysine (CML) is formed during glycation reactions (synonym, Maillard reaction). CML is degraded by the human colonic microbiota, but nothing is known about the formation of particular metabolites. In the present study, six probiotic E. coli strains were incubated with CML in the presence or absence of oxygen in either minimal or nutrient-rich medium. CML was degraded by all strains only in the presence of oxygen. HPLC-MS/MS was applied for identification of metabolites of CML. For the first time, three bacterial metabolites of CML have been identified, namely N-carboxymethylcadaverine (CM-CAD), N-carboxymethylaminopentanoic acid (CM-APA), and the N-carboxymethyl-Delta(1)-piperideinium ion. During 48 h of incubation of CML with five different E. coli strains in minimal medium in the presence of oxygen, 37-66% of CML was degraded, while CM-CAD (1.5-8.4% of the initial CML dose) and CM-APA (0.04-0.11% of the initial CML dose) were formed linearly. Formation of the metabolites is enhanced when dipeptide-bound CML is applied, indicating that transport phenomena may play an important role in the "handling" of the compound by microorganisms.

  DOI：

  10.1021/acs.jafc.8b06748
• 作为产物：
  描述：

  N-(5-氨基戊基)氨基甲酸叔丁酯 、 乙醛酸 在 palladium 10% on activated carbon 、 氢气 作用下， 以 水 为溶剂， 生成 N-{5-[(tert-Butoxycarbonyl)amino]pentyl}glycine
  参考文献：
  名称：

  Metabolization of the Advanced Glycation End ProductN-ε-Carboxymethyllysine (CML) by Different ProbioticE. coliStrains

  摘要：

  N-epsilon-Carboxymethyllysine (CML) is formed during glycation reactions (synonym, Maillard reaction). CML is degraded by the human colonic microbiota, but nothing is known about the formation of particular metabolites. In the present study, six probiotic E. coli strains were incubated with CML in the presence or absence of oxygen in either minimal or nutrient-rich medium. CML was degraded by all strains only in the presence of oxygen. HPLC-MS/MS was applied for identification of metabolites of CML. For the first time, three bacterial metabolites of CML have been identified, namely N-carboxymethylcadaverine (CM-CAD), N-carboxymethylaminopentanoic acid (CM-APA), and the N-carboxymethyl-Delta(1)-piperideinium ion. During 48 h of incubation of CML with five different E. coli strains in minimal medium in the presence of oxygen, 37-66% of CML was degraded, while CM-CAD (1.5-8.4% of the initial CML dose) and CM-APA (0.04-0.11% of the initial CML dose) were formed linearly. Formation of the metabolites is enhanced when dipeptide-bound CML is applied, indicating that transport phenomena may play an important role in the "handling" of the compound by microorganisms.

  DOI：

  10.1021/acs.jafc.8b06748

文献信息

• Metabolization of the Advanced Glycation End Product<i>N</i>-ε-Carboxymethyllysine (CML) by Different Probiotic<i>E. coli</i>Strains
  作者：Michael Hellwig、Christian Auerbach、Nicole Müller、Pauline Samuel、Sophie Kammann、Falco Beer、Florian Gunzer、Thomas Henle

  DOI：10.1021/acs.jafc.8b06748

  日期：2019.2.20

  N-epsilon-Carboxymethyllysine (CML) is formed during glycation reactions (synonym, Maillard reaction). CML is degraded by the human colonic microbiota, but nothing is known about the formation of particular metabolites. In the present study, six probiotic E. coli strains were incubated with CML in the presence or absence of oxygen in either minimal or nutrient-rich medium. CML was degraded by all strains only in the presence of oxygen. HPLC-MS/MS was applied for identification of metabolites of CML. For the first time, three bacterial metabolites of CML have been identified, namely N-carboxymethylcadaverine (CM-CAD), N-carboxymethylaminopentanoic acid (CM-APA), and the N-carboxymethyl-Delta(1)-piperideinium ion. During 48 h of incubation of CML with five different E. coli strains in minimal medium in the presence of oxygen, 37-66% of CML was degraded, while CM-CAD (1.5-8.4% of the initial CML dose) and CM-APA (0.04-0.11% of the initial CML dose) were formed linearly. Formation of the metabolites is enhanced when dipeptide-bound CML is applied, indicating that transport phenomena may play an important role in the "handling" of the compound by microorganisms.