2-tert-butoxycarbonylamino-3-[4-(2-tert-butoxycarbonylamino-2-methoxycarbonylethylsulfanyl)-2,5-dioxopyrrolidin-3-ylsulfanyl]propionic acid methyl ester | 1207982-89-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-tert-butoxycarbonylamino-3-[4-(2-tert-butoxycarbonylamino-2-methoxycarbonylethylsulfanyl)-2,5-dioxopyrrolidin-3-ylsulfanyl]propionic acid methyl ester
• CAS: 1207982-89-5
• 化学式: C₂₂H₃₅N₃O₁₀S₂
• 分子量: 565.666
• InChiKey: MXLWBMVBFPVFGY-FEPKRQSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  175.43
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  3-溴-1H-吡咯-2,5-二酮 、 N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以94%的产率得到2-tert-butoxycarbonylamino-3-[4-(2-tert-butoxycarbonylamino-2-methoxycarbonylethylsulfanyl)-2,5-dioxopyrrolidin-3-ylsulfanyl]propionic acid methyl ester
  参考文献：
  名称：

  Protein Modification, Bioconjugation, and Disulfide Bridging Using Bromomaleimides

  摘要：

  The maleimide motif is widely used for the selective chemical modification of cysteine residues in proteins Despite widespread utilization, there are some potential limitations, including the irreversible nature of the reaction and, hence, the modification and the number of attachment positions. We conceived of a new class of maleimide which would address some of these limitations and provide new opportunities for protein modification. We report herein the use of mono- and dibromomaleimides for reversible cysteine modification and illustrate this on the SH2 domain of the Grb2 adaptor protein (L111C) After initial modification of a protein with a bromo- or dibromomaleimide, it is possible to add an equivalent of a second thiol to give further boconjugation, demonstrating that bromomaleimides offer opportunities for up to three points of attachment The resultant protein-maleimide products can be cleaved to regenerate the unmodified protein by addition of a phosphine or a large excess of a thiol Furthermore, dibromomaleimide can insert into a disulfide bond, forming a maleimide bridge, and this is illustrated on the peptide hormone somatostatin Fluorescein-labeled dibromomaleimide is synthesized and inserted into the disulfide to construct a fluorescent somatostatin analogue These results highlight the significant potential for this new class of reagents in protein modification.

  DOI：

  10.1021/ja908610s