5'-O-(aspartylsulfamoyl)adenosine

• 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: 5'-O-(aspartylsulfamoyl)adenosine
• 英文别名: 3-amino-4-[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}sulfonyl)amino]-4-oxobutanoic acid；3-amino-4-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxysulfonylamino]-4-oxobutanoic acid
• 化学式: C₁₄H₁₉N₇O₉S
• 分子量: 461.412
• InChiKey: KMRBRMHHDAUXAY-FEYRHXAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.5
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  264
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  5'-O-(aspartylsulfamoyl)adenosine 、 乙酰辅酶A 在 recombinant Escherichia coli MccE protein C-terminal domain 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  MccE Provides Resistance to Protein Synthesis Inhibitor Microcin C by Acetylating the Processed Form of the Antibiotic

  摘要：

  The heptapeptide-nucleotide microcin C (McC) is a potent inhibitor of enteric bacteria growth. McC is excreted from producing cells by the MccC transporter. The residual McC that remains in the producing cell can be processed by cellular amino-peptidases with the release of a non-hydrolyzable aspartyl-adenylate, a strong inhibitor of aspartyl-tRNA synthetase. Accumulation of processed McC inside producing cells should therefore lead to translation inhibition and cessation of growth. Here, we show that a product of another gene of the McC biosynthetic cluster, mccE, acetylates processed McC and converts it into a non-toxic compound. MccE also makes Escherichia coli resistant to albomycin, a Trojan horse inhibitor unrelated to McC that, upon processing, gives rise to a serine coupled to a thioxylofuranosyl pyrimidine, an inhibitor of seryl-tRNA synthetase. We speculate that MccE and related cellular acetyltransferases of the Rim family may detoxify various aminoacyl-nucleotides, either exogenous or those generated inside the cell.

  DOI：

  10.1074/jbc.m109.080192

文献信息

• MccE Provides Resistance to Protein Synthesis Inhibitor Microcin C by Acetylating the Processed Form of the Antibiotic
  作者：Maria Novikova、Teymur Kazakov、Gaston H. Vondenhoff、Ekaterina Semenova、Jef Rozenski、Anastasija Metlytskaya、Inna Zukher、Anton Tikhonov、Arthur Van Aerschot、Konstantin Severinov

  DOI：10.1074/jbc.m109.080192

  日期：2010.4

  The heptapeptide-nucleotide microcin C (McC) is a potent inhibitor of enteric bacteria growth. McC is excreted from producing cells by the MccC transporter. The residual McC that remains in the producing cell can be processed by cellular amino-peptidases with the release of a non-hydrolyzable aspartyl-adenylate, a strong inhibitor of aspartyl-tRNA synthetase. Accumulation of processed McC inside producing cells should therefore lead to translation inhibition and cessation of growth. Here, we show that a product of another gene of the McC biosynthetic cluster, mccE, acetylates processed McC and converts it into a non-toxic compound. MccE also makes Escherichia coli resistant to albomycin, a Trojan horse inhibitor unrelated to McC that, upon processing, gives rise to a serine coupled to a thioxylofuranosyl pyrimidine, an inhibitor of seryl-tRNA synthetase. We speculate that MccE and related cellular acetyltransferases of the Rim family may detoxify various aminoacyl-nucleotides, either exogenous or those generated inside the cell.