Fmoc-Cys(MBom)-OH | 1370213-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Cys(MBom)-OH
• 英文别名: Fmoc-Cys(MBom)；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methoxyphenyl)methoxymethylsulfanyl]propanoic acid
• CAS: 1370213-71-0
• 化学式: C₂₇H₂₇NO₆S
• 分子量: 493.58
• InChiKey: WXYOFBYGJGHYPI-VWLOTQADSA-N

物化性质

• 沸点：
  699.7±55.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Fmoc-甘氨酸 、 Fmoc-Cys(MBom)-OH 、 Fmoc-L-苯丙氨酸 在 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) 、 N,N-二异丙基乙胺 、 6-氯-1-羟基苯并三氮唑 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 H-Gly-Cys-Phe-NH₂
  参考文献：
  名称：

  4-Methoxybenzyloxymethyl Group, a Racemization-Resistant Protecting Group for Cysteine in Fmoc Solid Phase Peptide Synthesis

  摘要：

  The 4-methoxybenzyloxymethyl (MBom) group was introduced for sulfhydryl protection of Cys in combination with Fmoc chemistry. The MBom group proved to substantially suppress racemization of Cys during its incorporation mediated by phosphonium or uronium reagents. Furthermore, this group was found to significantly reduce racemization of the C-terminal Cys linked to a hydroxyl resin during repetitive base treatment, in comparison with the usually used trityl (Trt) and acetamidomethyl (Acm) groups.

  DOI：

  10.1021/ol300592w
• 作为产物：
  描述：

  Fmoc-Cys(MBom)-OAllyl 在 四(三苯基膦)钯 、 5,5-二甲基-1,3-环己二酮 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以76%的产率得到Fmoc-Cys(MBom)-OH
  参考文献：
  名称：

  4-Methoxybenzyloxymethyl Group, a Racemization-Resistant Protecting Group for Cysteine in Fmoc Solid Phase Peptide Synthesis

  摘要：

  The 4-methoxybenzyloxymethyl (MBom) group was introduced for sulfhydryl protection of Cys in combination with Fmoc chemistry. The MBom group proved to substantially suppress racemization of Cys during its incorporation mediated by phosphonium or uronium reagents. Furthermore, this group was found to significantly reduce racemization of the C-terminal Cys linked to a hydroxyl resin during repetitive base treatment, in comparison with the usually used trityl (Trt) and acetamidomethyl (Acm) groups.

  DOI：

  10.1021/ol300592w

文献信息

• Evaluation of acid‐labile <scp> <i>S</i> </scp> ‐protecting groups to prevent Cys racemization in Fmoc solid‐phase peptide synthesis
  作者：Hajime Hibino、Yasuyoshi Miki、Yuji Nishiuchi

  DOI：10.1002/psc.2585

  日期：2014.1

  also the former method cannot reduce racemization of Cys(Trt) to an acceptable level (<1.0%) even when the preactivation procedure is omitted. Here, the 4,4′‐dimethoxydiphenylmethyl and 4‐methoxybenzyloxymethyl groups were demonstrated to be acid‐labile S‐protecting groups that can suppress racemization of Cys to an acceptable level (<1.0%) when the respective Fmoc derivatives are incorporated via the

  基于鏻和脲盐的试剂能够实现高效和有效的偶联反应，并且在肽化学中是必不可少的，尤其是在机器辅助 SPPS 中。然而，在叔胺存在下用这些试剂进行活化和偶联步骤后，已知 Cys 的 Fmoc 衍生物在其掺入过程中显着外消旋化。为了避免这种副反应，推荐使用一种由鏻/脲试剂与弱碱（如 2,4,6-三甲基吡啶）介导的偶联方法，该方法比通常使用的 DIEA 或碳二亚胺。然而，这些方法明显不如用于 SPPS 的标准方案，即在 DMF 中与鏻或脲试剂/DIEA 偶联的 1 分钟预活化程序，在偶联效率方面，即使省略了预活化程序，前一种方法也不能将 Cys(Trt) 的外消旋化降低到可接受的水平 (<1.0%)。在这里，4,4'-二甲氧基二苯基甲基和 4-甲氧基苄氧基甲基被证明是酸不稳定的当相应的 Fmoc 衍生物在 DMF 中的 DIEA 的帮助下通过鏻或脲试剂的标准 SPPS 方案加入时，S-保护基团可以将
• 4-Methoxybenzyloxymethyl Group, a Racemization-Resistant Protecting Group for Cysteine in Fmoc Solid Phase Peptide Synthesis
  作者：Hajime Hibino、Yuji Nishiuchi

  DOI：10.1021/ol300592w

  日期：2012.4.6

  The 4-methoxybenzyloxymethyl (MBom) group was introduced for sulfhydryl protection of Cys in combination with Fmoc chemistry. The MBom group proved to substantially suppress racemization of Cys during its incorporation mediated by phosphonium or uronium reagents. Furthermore, this group was found to significantly reduce racemization of the C-terminal Cys linked to a hydroxyl resin during repetitive base treatment, in comparison with the usually used trityl (Trt) and acetamidomethyl (Acm) groups.