Boc-L-Cys(S-oNBn)-NH2 | 476639-83-5

• 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: Boc-L-Cys(S-oNBn)-NH2
• 英文别名: tert-butyl N-[(2R)-1-amino-3-[(2-nitrophenyl)methylsulfanyl]-1-oxopropan-2-yl]carbamate
• CAS: 476639-83-5
• 化学式: C₁₅H₂₁N₃O₅S
• 分子量: 355.415
• InChiKey: AEFUNGOHZJUVIQ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-L-Cys(S-oNBn)-NH2 在 photolysis buffer 作用下， 反应 2.0h， 以100%的产率得到N^α-Boc-cystamine
  参考文献：
  名称：

  Peptide−Small Molecule Hybrids via Orthogonal Deprotection−Chemoselective Conjugation to Cysteine-Anchored Scaffolds. A Model Study

  摘要：

  [GRAPHICS]The feasibility of an orthogonal deprotection-conjugation protocol, holding the promise of libraries of functionally diverse chemical probes attached to cysteine-anchored peptide scaffolds, has been explored with a model system. The necessary tools for assembly of the hybrid libraries have been prepared and the tandem procedure optimized. S-Alkylation and S-sulfenylation are featured as the chemoselective ligation reactions.

  DOI：

  10.1021/ol026736d
• 作为产物：
  描述：

  2-硝基苄氯 在 sodium hydroxide 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 Boc-L-Cys(S-oNBn)-NH2
  参考文献：
  名称：

  Peptide−Small Molecule Hybrids via Orthogonal Deprotection−Chemoselective Conjugation to Cysteine-Anchored Scaffolds. A Model Study

  摘要：

  [GRAPHICS]The feasibility of an orthogonal deprotection-conjugation protocol, holding the promise of libraries of functionally diverse chemical probes attached to cysteine-anchored peptide scaffolds, has been explored with a model system. The necessary tools for assembly of the hybrid libraries have been prepared and the tandem procedure optimized. S-Alkylation and S-sulfenylation are featured as the chemoselective ligation reactions.

  DOI：

  10.1021/ol026736d

文献信息

• Peptide−Small Molecule Hybrids via Orthogonal Deprotection−Chemoselective Conjugation to Cysteine-Anchored Scaffolds. A Model Study
  作者：Amos B. Smith、Sergey N. Savinov、Uma V. Manjappara、Irwin M. Chaiken

  DOI：10.1021/ol026736d

  日期：2002.11.1

  [GRAPHICS]The feasibility of an orthogonal deprotection-conjugation protocol, holding the promise of libraries of functionally diverse chemical probes attached to cysteine-anchored peptide scaffolds, has been explored with a model system. The necessary tools for assembly of the hybrid libraries have been prepared and the tandem procedure optimized. S-Alkylation and S-sulfenylation are featured as the chemoselective ligation reactions.