Fmoc-Cys(MBom)-OAllyl | 1370213-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Cys(MBom)-OAllyl
• CAS: 1370213-74-3
• 化学式: C₃₀H₃₁NO₆S
• 分子量: 533.645
• InChiKey: SNRBHBVYPWXMFP-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  38.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-[(氯甲氧基)甲基]-4-甲氧基苯 、 Fmoc-Cys-OAllyl 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到Fmoc-Cys(MBom)-OAllyl
  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