(S)-2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-3-{2-([4-{(tert-butyldiphenylsilyl)oxy}benzyl]oxy)-4,6-dimethylphenyl}-3-methylbutanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-3-{2-([4-{(tert-butyldiphenylsilyl)oxy}benzyl]oxy)-4,6-dimethylphenyl}-3-methylbutanoic acid
• 英文别名: (2S)-3-[2-[[4-[tert-butyl(diphenyl)silyl]oxyphenyl]methoxy]-4,6-dimethylphenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoic acid
• 化学式: C₅₁H₅₃NO₆Si
• 分子量: 804.07
• InChiKey: RCKZIURMKIYYTG-QZNUWAOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.09
• 重原子数：
  59
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-N-Fmoc-6-叠氮基己酸 、 2-chlorotrityl resin 、 (S)-2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-3-{2-([4-{(tert-butyldiphenylsilyl)oxy}benzyl]oxy)-4,6-dimethylphenyl}-3-methylbutanoic acid 、 D-生物素 、 Fmoc-3-(氨基氧基)乙酸 、 [2-[2-(Fmoc-氨基)乙氧基]乙氧基]乙酸 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 以12%的产率得到
  参考文献：
  名称：

  Development of a fluoride-responsive amide bond cleavage device that is potentially applicable to a traceable linker

  摘要：

  A fluoride-responsive (FR) amino acid that induces amide bond cleavage upon the addition of a fluoride was developed, and it was applied to an FR traceable linker. By the use of an allcyne-containing peptide as a model of an alkynylated target protein of a bioactive compound, introduction of the FR traceable linker onto the peptide was achieved. Subsequent fluoride-induced cleavage of the linker followed by labeling of the released peptide derivative was also conducted to examine the potential applicability of the FR traceable linker to the enrichment and labeling of allcynylated target molecules. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.110
• 作为产物：
  描述：

  (4-((tert-butyldiphenylsilyl)oxy)phenyl)methanol 在 2,6-二甲基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 草酰氯 、 三丁基膦 、 叔丁基二甲硅基三氟甲磺酸酯 、 水 、 sodium carbonate 、 溶剂黄146 、 二甲基亚砜 、 N,N,N' ,N'-tetramethylazodicarboxamide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 18.0h， 生成 (S)-2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-3-{2-([4-{(tert-butyldiphenylsilyl)oxy}benzyl]oxy)-4,6-dimethylphenyl}-3-methylbutanoic acid
  参考文献：
  名称：

  Development of a fluoride-responsive amide bond cleavage device that is potentially applicable to a traceable linker

  摘要：

  A fluoride-responsive (FR) amino acid that induces amide bond cleavage upon the addition of a fluoride was developed, and it was applied to an FR traceable linker. By the use of an allcyne-containing peptide as a model of an alkynylated target protein of a bioactive compound, introduction of the FR traceable linker onto the peptide was achieved. Subsequent fluoride-induced cleavage of the linker followed by labeling of the released peptide derivative was also conducted to examine the potential applicability of the FR traceable linker to the enrichment and labeling of allcynylated target molecules. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.110

文献信息

• Development of a fluoride-responsive amide bond cleavage device that is potentially applicable to a traceable linker
  作者：Jun Yamamoto、Nami Maeda、Chiaki Komiya、Tomohiro Tanaka、Masaya Denda、Koji Ebisuno、Wataru Nomura、Hirokazu Tamamura、Youichi Sato、Aiko Yamauchi、Akira Shigenaga、Akira Otaka

  DOI：10.1016/j.tet.2014.05.110

  日期：2014.8

  A fluoride-responsive (FR) amino acid that induces amide bond cleavage upon the addition of a fluoride was developed, and it was applied to an FR traceable linker. By the use of an allcyne-containing peptide as a model of an alkynylated target protein of a bioactive compound, introduction of the FR traceable linker onto the peptide was achieved. Subsequent fluoride-induced cleavage of the linker followed by labeling of the released peptide derivative was also conducted to examine the potential applicability of the FR traceable linker to the enrichment and labeling of allcynylated target molecules. (C) 2014 Elsevier Ltd. All rights reserved.