[(1S)-1-acetamido-2-(1-naphthyl)ethyl]boronic acid | 173860-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(1S)-1-acetamido-2-(1-naphthyl)ethyl]boronic acid
• 英文别名: [(1S)-1-acetamido-2-naphthalen-1-ylethyl]boronic acid
• CAS: 173860-24-7
• 化学式: C₁₄H₁₆BNO₃
• 分子量: 257.097
• InChiKey: LVTLNDJMGVBXSL-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(1S)-1-acetamido-2-(1-naphthyl)ethyl]boronic acid 、 二乙醇胺 以 异丙醇 为溶剂， 以40%的产率得到dietanolamine [(1S)-1-acetamido-2-(1-naphthyl)ethyl]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
• 作为产物：
  描述：

  N-((S)-2-(naphthalen-1-yl)-1-((3aR,4R,6R,7aS)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)acetamide 在 三氯化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 生成 [(1S)-1-acetamido-2-(1-naphthyl)ethyl]boronic acid
  参考文献：
  名称：

  Synthesis and carbohydrate binding studies of fluorescent α-amidoboronic acids and the corresponding bisboronic acids

  摘要：

  Fluorescent boronic acids are very useful for the design and synthesis of carbohydrate sensors. In an earlier communication, we first described the effort of developing water soluble fluorescent alpha-amidoboronic acids, which change fluorescence upon sugar binding. In this report, we describe a general method of functionalizing such boronic acids and their applications in the preparation of bis-alpha-amidoboronic acids with significantly enhanced binding for oligosaccharides as compared to their monoboronic acid counterparts. The advantages of good water solubility, easy modification to generate diversity, and modularity in synthesis will make alpha-amidoboronic acids very useful building blocks for future synthesis of boronic acid-based fluorescent sensors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.01.017

文献信息

• Probing the Specificity of the Serine Proteases Subtilisin Carlsberg and α-Chymotrypsin with Enantiomeric 1-Acetamido Boronic Acids. An Unexpected Reversal of the Normal “<scp>l</scp>”-Stereoselectivity Preference
  作者：Valeri Martichonok、J. Bryan Jones

  DOI：10.1021/ja952816j

  日期：1996.1.1

  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.
• Synthesis and carbohydrate binding studies of fluorescent α-amidoboronic acids and the corresponding bisboronic acids
  作者：Shan Jin、Chunyuan Zhu、Yunfeng Cheng、Minyong Li、Binghe Wang

  DOI：10.1016/j.bmc.2010.01.017

  日期：2010.2

  Fluorescent boronic acids are very useful for the design and synthesis of carbohydrate sensors. In an earlier communication, we first described the effort of developing water soluble fluorescent alpha-amidoboronic acids, which change fluorescence upon sugar binding. In this report, we describe a general method of functionalizing such boronic acids and their applications in the preparation of bis-alpha-amidoboronic acids with significantly enhanced binding for oligosaccharides as compared to their monoboronic acid counterparts. The advantages of good water solubility, easy modification to generate diversity, and modularity in synthesis will make alpha-amidoboronic acids very useful building blocks for future synthesis of boronic acid-based fluorescent sensors. Published by Elsevier Ltd.