3'-deoxy-N⁶,N⁶-dimethyl-3'-(L-2-hydroxyglutaryl-amido)adenosine | 1016893-80-3

• 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: 3'-deoxy-N⁶,N⁶-dimethyl-3'-(L-2-hydroxyglutaryl-amido)adenosine
• 英文别名: (4S)-5-[[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]amino]-4-hydroxy-5-oxopentanoic acid
• CAS: 1016893-80-3
• 化学式: C₁₇H₂₄N₆O₇
• 分子量: 424.414
• InChiKey: QSZWEGDXGJIOFM-SAIRCXCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  183
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3'-deoxy-N6,N6-dimethyl-3'-(L-5-oxo-2-tetrahydrofurancarboxamide)adenosine 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.25h， 以91%的产率得到3'-deoxy-N⁶,N⁶-dimethyl-3'-(L-2-hydroxyglutaryl-amido)adenosine
  参考文献：
  名称：

  Inhibition of Helicobacter pylori Aminoacyl-tRNA Amidotransferase by Puromycin Analogues

  摘要：

  Recent genomic studies revealed the absence of glutaminyl-tRNA synthetase and/or asparaginyl-tRNA synthetase in many bacteria and archaea. The survival of microorganisms missing one or both of these essential enzymes implies an alternative pathway for the formation of Gln-tRNA(Gln) and Asn-tRNA(Asn). This indirect pathway involves misacylation of tRNA(Gln) with Glu (or tRNA(Asn) with Asp) by a nondiscriminating synthetase and subsequent transamidation of the misacylated aa-tRNA by an amidotransferase. Analogues of the natural product puromycin have been developed to inhibit this class of enzymes which has been only recently investigated at the mechanistic and structural levels. The widespread use of the indirect transamidation pathway among prominent human pathogens and its absence in the cytosol of mammalian cells identify aminoacyl-tRNA amidotransferases as an interesting target for the development of antimicrobial agents with a novel mode of action. These mechanism-based inhibitors will provide useful probes for further mechanistic investigations and ligands for X-ray crystallography.

  DOI：

  10.1021/ja7100714