diethanolamine [(1S)-1-acetamidoethyl]boronate | 173860-36-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: diethanolamine [(1S)-1-acetamidoethyl]boronate
• 英文别名: N-[(1S)-1-(1,3,6,2-dioxazaborocan-2-yl)ethyl]acetamide
• CAS: 173860-36-1
• 化学式: C₈H₁₇BN₂O₃
• 分子量: 200.046
• InChiKey: YKHXEWKBRTZCOB-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  59.59
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  [(1S)-1-acetamidoethyl]boronic acid 、 二乙醇胺 以 异丙醇 为溶剂， 以55%的产率得到diethanolamine [(1S)-1-acetamidoethyl]boronate
  参考文献：
  名称：

  Probing the Specificity of the Serine Proteases Subtilisin Carlsberg and α-Chymotrypsin with Enantiomeric 1-Acetamido Boronic Acids. An Unexpected Reversal of the Normal “l”-Stereoselectivity Preference

  摘要：

  Enantiomeric 1-acetamido boronic acids, which are N-acetyl transition state analog inhibitor analogs of L- and D-forms of the amino acids alanine, phenylalanine, p-fluorophenylalanine, p-chlorophenylalanine, and 1-naphthylalanine, have been evaluated as inhibitors of the serine proteases subtilisin Carlsberg (SC) and alpha-chymotrypsin (CT). All of the boronic acids are powerful competitive inhibitors of both enzymes, with, as expected, the L-enantiomers being generally more potent than the D-enantiomers. However, a dramatic reversal of the normal stereoselectivity preference was observed in the inhibition of CT by [1-acetamido-2-(1-naphthyl)ethyl]boronic acid, with the D-enantiomer becoming a 25-fold more potent inhibitor than the L-enantiomer. Furthermore, the K-I of 127 nM for CT inhibition by this D-enantiomer is the lowest of any of the boronic acids evaluated. Molecular modeling analyses of the possible binding modes of the inhibitors suggest that the stereoselectivity reversal is due to S-1-pocket orientations of naphthyl groups that are different from those of the aromatic side chains of the phenylalanine analogs.

  DOI：

  10.1021/ja952816j