N-BSMOC-L-色氨酸 | 197245-27-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 色氨酸类衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: N-BSMOC-L-色氨酸
• 中文别名: N-Bsmoc-L-色氨酸
• 英文名称: Bsmoc-Trp-OH
• 英文别名: N-Bsmoc-L-tryptophan；(2S)-2-[(1,1-dioxo-1-benzothiophen-2-yl)methoxycarbonylamino]-3-(1H-indol-3-yl)propanoic acid
• CAS: 197245-27-5
• 化学式: C₂₁H₁₈N₂O₆S
• 分子量: 426.45
• InChiKey: UILOLDADSJLWEJ-SFHVURJKSA-N

物化性质

• 熔点：
  80-106℃
• 沸点：
  768.6±60.0 °C(Predicted)
• 密度：
  1.501±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  避还原剂

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 安全说明：
  S22,S24/25
• 储存条件：
  保存方法：在干燥、阴凉且密闭的环境中存放，应保持温度在5°C以下。

反应信息

• 作为反应物：
  描述：

  N-BSMOC-L-色氨酸 在 吡啶 、 三聚氟氰 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以80%的产率得到Bsmoc-Trp-F
  参考文献：
  名称：

  The 1,1-Dioxobenzo[b]thiophene-2-ylmethyloxycarbonyl (Bsmoc) Amino-Protecting Group

  摘要：

  Full details are presented for use of the Bsmoc amino-protecting group for both solid phase and rapid continuous solution syntheses. Application to the latter methodology represents a significant improvement over the corresponding Fmoc-based method for rapid solution synthesis due to the opportunity to use water or saturated sodium-chloride solution rather than an acidic phosphate buffer to remove all byproducts, with consequent cleaner phase separation and higher yields of the growing peptide. Comparison of the Bsmoc and Bspoc functions showed that the former, because of steric hindrance, does not suffer from the competitive or premature deblocking observed with the Bspoc system. Because of its incorporation of a styrene chromophore, resin loading of Bsmoc amino acids could be followed as has previously been shown for the Fmoc analogues. Applications of Bsmoc chemistry to peptide sequences incorporating the base sensitive Asp-Gly unit gave less contamination due to aminosuccinimide formation than comparable syntheses involving standard Fmoc chemistry because a weaker or less concentrated base could be used in the deblocking step. Experimental details are presented for building up peptides in solution via the continuous methodology. Deblockings involved the use of insoluble piperazino silica as well as the polyamine TAEA which simplified aqueous separation of the growing, but nonisolated peptide product, from excess acylating agent and other side products formed in the deblocking process. By the appropriate choice of base, one can act selectively at either site of a molecule which incorporates both beta-elimination and Michael acceptor sites as protective units (Bsmoc vs Fm and Fmoc vs Bsm).

  DOI：

  10.1021/jo982140l
• 作为产物：
  描述：

  benzothiophen-2-yllithium 在 sodium perborate 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 20.75h， 生成 N-BSMOC-L-色氨酸
  参考文献：
  名称：

  The 1,1-Dioxobenzo[b]thiophene-2-ylmethyloxycarbonyl (Bsmoc) Amino-Protecting Group

  摘要：

  Full details are presented for use of the Bsmoc amino-protecting group for both solid phase and rapid continuous solution syntheses. Application to the latter methodology represents a significant improvement over the corresponding Fmoc-based method for rapid solution synthesis due to the opportunity to use water or saturated sodium-chloride solution rather than an acidic phosphate buffer to remove all byproducts, with consequent cleaner phase separation and higher yields of the growing peptide. Comparison of the Bsmoc and Bspoc functions showed that the former, because of steric hindrance, does not suffer from the competitive or premature deblocking observed with the Bspoc system. Because of its incorporation of a styrene chromophore, resin loading of Bsmoc amino acids could be followed as has previously been shown for the Fmoc analogues. Applications of Bsmoc chemistry to peptide sequences incorporating the base sensitive Asp-Gly unit gave less contamination due to aminosuccinimide formation than comparable syntheses involving standard Fmoc chemistry because a weaker or less concentrated base could be used in the deblocking step. Experimental details are presented for building up peptides in solution via the continuous methodology. Deblockings involved the use of insoluble piperazino silica as well as the polyamine TAEA which simplified aqueous separation of the growing, but nonisolated peptide product, from excess acylating agent and other side products formed in the deblocking process. By the appropriate choice of base, one can act selectively at either site of a molecule which incorporates both beta-elimination and Michael acceptor sites as protective units (Bsmoc vs Fm and Fmoc vs Bsm).

  DOI：

  10.1021/jo982140l

文献信息

• The 1,1-Dioxobenzo[<i>b</i>]thiophene-2-ylmethyloxycarbonyl (Bsmoc) Amino-Protecting Group
  作者：Louis A. Carpino、Mohamed Ismail、George A. Truran、E. M. E. Mansour、Shin Iguchi、Dumitru Ionescu、Ayman El-Faham、Christoph Riemer、Ralf Warrass

  DOI：10.1021/jo982140l

  日期：1999.6.1

  Full details are presented for use of the Bsmoc amino-protecting group for both solid phase and rapid continuous solution syntheses. Application to the latter methodology represents a significant improvement over the corresponding Fmoc-based method for rapid solution synthesis due to the opportunity to use water or saturated sodium-chloride solution rather than an acidic phosphate buffer to remove all byproducts, with consequent cleaner phase separation and higher yields of the growing peptide. Comparison of the Bsmoc and Bspoc functions showed that the former, because of steric hindrance, does not suffer from the competitive or premature deblocking observed with the Bspoc system. Because of its incorporation of a styrene chromophore, resin loading of Bsmoc amino acids could be followed as has previously been shown for the Fmoc analogues. Applications of Bsmoc chemistry to peptide sequences incorporating the base sensitive Asp-Gly unit gave less contamination due to aminosuccinimide formation than comparable syntheses involving standard Fmoc chemistry because a weaker or less concentrated base could be used in the deblocking step. Experimental details are presented for building up peptides in solution via the continuous methodology. Deblockings involved the use of insoluble piperazino silica as well as the polyamine TAEA which simplified aqueous separation of the growing, but nonisolated peptide product, from excess acylating agent and other side products formed in the deblocking process. By the appropriate choice of base, one can act selectively at either site of a molecule which incorporates both beta-elimination and Michael acceptor sites as protective units (Bsmoc vs Fm and Fmoc vs Bsm).