N2-((R)-1-carboxyethyl)-2'-deoxyguanine | 1265223-47-9

• 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: N2-((R)-1-carboxyethyl)-2'-deoxyguanine
• 英文别名: (2R)-2-[(6-oxo-1,7-dihydropurin-2-yl)amino]propanoic acid
• CAS: 1265223-47-9
• 化学式: C₈H₉N₅O₃
• 分子量: 223.191
• InChiKey: YCCGSWHBNBAHIT-GSVOUGTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N2-((R)-1-carboxyethyl)guanosine 5'-monophosphate 在 盐酸 、 水 、 sodium hydroxide 作用下， 反应 2.5h， 生成 N2-((R)-1-carboxyethyl)-2'-deoxyguanine
  参考文献：
  名称：

  Discovery of N²-(1-Carboxyethyl)guanosine 5′-Monophosphate as an Umami-Enhancing Maillard-Modified Nucleotide in Yeast Extracts

  摘要：

  Sensory-guided fractionation of a commercial yeast extract involving medium-pressure RP-18 chromatography and ion-pair chromatography, followed by LC-MS/MS, LC-TOF-MS, 1D/2D-NMR, and CD spectroscopy, led to the discovery of the previously not reported umami-enhancing nucleotide diastereomers (R)- and (S)-N-2-(1-carboxyethyl)guanosine 5'-monophosphate. Model experiments confirmed the formation of these diastereomers by a Maillard-type glycation of guanosine 5'-monophosphate with dihydroxyacetone and glyceraldehyde, respectively. Sensory studies revealed umami recognition threshold concentrations of 0.19 and 0.85 mmol/L for the (S)- and (R)-configured diastereomers, respectively, and demonstrated the taste-enhancing activity of these nucleotides on monosodium L-glutamate solutions.

  DOI：

  10.1021/jf102899j