N-allyloxycarbonyl-L-methionyl-L-tyrosyl-L-(3-bromo-alanine) methyl ester | 852325-27-0

• 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: N-allyloxycarbonyl-L-methionyl-L-tyrosyl-L-(3-bromo-alanine) methyl ester
• 英文别名: Alloc-Met-Tyr-Ala(Br)-OMe；methyl (2R)-3-bromo-2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(2S)-4-methylsulfanyl-2-(prop-2-enoxycarbonylamino)butanoyl]amino]propanoyl]amino]propanoate
• CAS: 852325-27-0
• 化学式: C₂₂H₃₀BrN₃O₇S
• 分子量: 560.466
• InChiKey: DKJNHRQXOJVXHZ-BZSNNMDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  168
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-allyloxycarbonyl-L-methionyl-L-tyrosyl-L-(3-bromo-alanine) methyl ester 、 硫代棕榈酸 在 sodium acetate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以76%的产率得到N-allyloxycarbonyl-L-methionyl-L-tyrosyl-[(S-palmitoyl)-L-cysteine] methyl ester
  参考文献：
  名称：

  Reversed Approach to S-Farnesylation and S-Palmitoylation:  Application to an Efficient Synthesis of the C-Terminus of Lipidated Human N-Ras Hexapeptide

  摘要：

  A general reversed approach is described to synthesize S-palmitoylated and S-farnesylated peptides via S(N)2 displacement of bromide by reaction of a thiol group containing lipid as nucleophile with bromoalanine-containing peptides as electrophile. By employing this approach, lipidated peptides, including characteristic partial structures of human Ras peptides, were synthesized in good yields. This method gives access to farnesylated, palmitoylated, and doubly lipidated peptides.

  DOI：

  10.1021/jo0482357
• 作为产物：
  描述：

  3-bromoalanine methyl estet trifluoroacetate 、 Alloc-Met-Tyr-OH 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以310 mg的产率得到N-allyloxycarbonyl-L-methionyl-L-tyrosyl-L-(3-bromo-alanine) methyl ester
  参考文献：
  名称：

  Reversed Approach to S-Farnesylation and S-Palmitoylation:  Application to an Efficient Synthesis of the C-Terminus of Lipidated Human N-Ras Hexapeptide

  摘要：

  A general reversed approach is described to synthesize S-palmitoylated and S-farnesylated peptides via S(N)2 displacement of bromide by reaction of a thiol group containing lipid as nucleophile with bromoalanine-containing peptides as electrophile. By employing this approach, lipidated peptides, including characteristic partial structures of human Ras peptides, were synthesized in good yields. This method gives access to farnesylated, palmitoylated, and doubly lipidated peptides.

  DOI：

  10.1021/jo0482357

文献信息

• Reversed Approach to <i>S</i>-Farnesylation and <i>S</i>-Palmitoylation:  Application to an Efficient Synthesis of the C-Terminus of Lipidated Human N-Ras Hexapeptide
  作者：Kandasamy Pachamuthu、Xiangming Zhu、Richard R. Schmidt

  DOI：10.1021/jo0482357

  日期：2005.4.1

  A general reversed approach is described to synthesize S-palmitoylated and S-farnesylated peptides via S(N)2 displacement of bromide by reaction of a thiol group containing lipid as nucleophile with bromoalanine-containing peptides as electrophile. By employing this approach, lipidated peptides, including characteristic partial structures of human Ras peptides, were synthesized in good yields. This method gives access to farnesylated, palmitoylated, and doubly lipidated peptides.