| 1235514-53-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1235514-53-0
• 化学式: C₅₅H₈₆N₂O₁₉
• 分子量: 1079.29
• InChiKey: OHPQROKMRHNYOJ-GCFWYILVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  76.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  291.49
• 氢给体数：
  7.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以23%的产率得到
  参考文献：
  名称：

  Amino acid and peptide derivatives of the tylosin family of macrolide antibiotics modified by aldehyde function

  摘要：

  Fourteen new functionally active amino acid and peptide derivatives of the antibiotics tylosin, desmycosin, and 5-O-mycaminosyltylonolide were synthesized in order to study the interaction of the growing polypeptide chain with the ribosomal tunnel. The conjugation of various amino acids and peptides with a macrolide aldehyde group was carried out by two methods: direct reductive amination with the isolation of the intermediate Schiff bases or through binding via oxime using the preliminarily obtained derivatives of 2-aminooxy-acetic acid.

  DOI：

  10.1134/s1068162010020159
• 作为产物：
  描述：

  L-酪氨酸 、 泰乐菌素 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Interplay between the Ribosomal Tunnel, Nascent Chain, and Macrolides Influences Drug Inhibition

  摘要：

  Accumulating evidence suggests that, during translation, nascent chains can form specific interactions with ribosomal exit tunnel to regulate translation and promote initial folding events. The clinically important macrolide antibiotics bind within the exit tunnel and inhibit translation by preventing progression of the nascent chain and inducing peptidyl-tRNA drop-off. Here, we have synthesized amino acid- and peptide-containing macrolides, which are used to demonstrate that distinct amino acids and peptides can establish interaction with components of the ribosomal tunnel and enhance the ribosome-binding and inhibitory properties of the macrolide drugs, consistent with the concept that the exit tunnel is not simply a Teflon-like channel. Surprisingly, we find that macrolide antibiotics do not inhibit translation of all nascent chains similarly, but rather exhibit polypeptide-specific inhibitory effects, providing a change to our general mechanistic understanding of macrolide inhibition.

  DOI：

  10.1016/j.chembiol.2010.04.008