3-[2-(3-boronophenyl)benzoxazol-5-yl]alanine methyl ester | 1402739-47-2

• 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: 3-[2-(3-boronophenyl)benzoxazol-5-yl]alanine methyl ester
• 英文别名: [3-[5-[(2S)-2-amino-3-methoxy-3-oxopropyl]-1,3-benzoxazol-2-yl]phenyl]boronic acid
• CAS: 1402739-47-2
• 化学式: C₁₇H₁₇BN₂O₅
• 分子量: 340.143
• InChiKey: JFGKJVPJMVBOLS-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.22
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-Boc-3-amino-L-tyrosine methyl ester 在 lead(IV) tetraacetate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 3-[2-(3-boronophenyl)benzoxazol-5-yl]alanine methyl ester
  参考文献：
  名称：

  3-[2-(Boronophenyl)benzoxazol-5-yl]alanine derivatives as fluorescent monosaccharide sensors

  摘要：

  Two 3-[2-(boronophenyl)benzoxazol-5-yl]alanine derivatives were synthesized and their potential application as fluorescent monosaccharide sensors was studied. It was found that both non-proteinogenic amino acids bound glucose and fructose at physiological pH, however, the latter much stronger. As a result they are selective sensors for fructose. Moreover, one of them (3-[2-(3-boronophenyl)benzoxazol-5-yl]alanine methyl ester) can be used to quickly distinguish, which monosaccharide is present in the solution because of the different character of fluorescence intensity changes (increase in the presence of fructose and decrease in the presence of glucose). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.085