puromycin

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: puromycin
• 英文别名: 9-{3'-deoxy-3'-[(4-methoxy-D-phenylalanyl)amino]-β-D-ribofuranosyl}-6-(N,N-dimethylamino)purine；N⁶-Dimethyl-3'-(α-amino-p-methoxyhydrocinnamamido)-3'-deoxyadenosine；3'-deoxy-N,N-dimethyl-3'-[(O-methyl-D-tyrosyl)amino]adenosine；(2R)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide
• 化学式: C₂₂H₂₉N₇O₅
• 分子量: 471.516
• InChiKey: RXWNCPJZOCPEPQ-FNQTVZJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  氨基核苷嘌呤霉素 在 哌啶 、 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 puromycin
  参考文献：
  名称：

  The Puromycin Route to Assess Stereo- and Regiochemical Constraints on Peptide Bond Formation in Eukaryotic Ribosomes

  摘要：

  We synthesized a series of puromycin analogues to probe the chemical specificity of the ribosome in an intact eukaryotic translation system. These studies reveal that both d-enantiomers and beta-amino acid analogues can be incorporated into protein, and provide a quantitative means to rank natural and unnatural residues. Modeling of a d-amino acid analogue into the 50S ribosomal subunit indicates that steric clash may provide part of the chiral discrimination. The data presented provide one metric of the chiral and regiospecificity of mammalian ribosomes.

  DOI：

  10.1021/ja034817e

文献信息

• The Puromycin Route to Assess Stereo- and Regiochemical Constraints on Peptide Bond Formation in Eukaryotic Ribosomes
  作者：Shelley R. Starck、Xin Qi、Brett N. Olsen、Richard W. Roberts

  DOI：10.1021/ja034817e

  日期：2003.7.1

  We synthesized a series of puromycin analogues to probe the chemical specificity of the ribosome in an intact eukaryotic translation system. These studies reveal that both d-enantiomers and beta-amino acid analogues can be incorporated into protein, and provide a quantitative means to rank natural and unnatural residues. Modeling of a d-amino acid analogue into the 50S ribosomal subunit indicates that steric clash may provide part of the chiral discrimination. The data presented provide one metric of the chiral and regiospecificity of mammalian ribosomes.