2'-(1-(benzyloxycarbonylamino)ethyl phosphonyl)adenosine | 802023-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(1-(benzyloxycarbonylamino)ethyl phosphonyl)adenosine
• CAS: 802023-20-7
• 化学式: C₂₀H₂₅N₆O₈P
• 分子量: 508.428
• InChiKey: CPCVWWQCKXNAEP-UVCRECLJSA-N

反应信息

• 作为反应物：
  描述：

  2'-(1-(benzyloxycarbonylamino)ethyl phosphonyl)adenosine 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以3.0 mg的产率得到adenosine-2'-(1-aminoethyl)phosphonate
  参考文献：
  名称：

  Inhibition of tRNA-dependent ligase MurM from Streptococcus pneumoniae by phosphonate and sulfonamide inhibitors

  摘要：

  Ligase MurM catalyses the addition of Ala from alanyl-tRNA(Ala), or Ser from seryl-tRNA(Ser), to lipid intermediate II in peptidoglycan biosynthesis in Streptococcus pneumoniae, and is a determinant of high-level penicillin resistance. Phosphorus-based transition state analogues were designed as inhibitors of the MurM-catalysed reaction. Phosphonamide analogues mimicking the attack of a lysine nucleophile upon Ala-tRNA(Ala) showed no inhibition of MurM, but adenosine 3'-phosphonate analogues showed inhibition of MurM, the most active being a 2'-deoxyadenosine analogue (IC50 100 mu M). Structure/function studies upon this analogue established that modi. cation of the amino group of the aminoalkylphosphonate resulted in loss of potency, and modi. cation of the adenosine 5'-hydroxyl group with either a t-butyl dimethyl silyl or a carbamate functional group resulted in loss of activity. A library of 48 aryl sulfonamides was also screened against MurM using a radiochemical assay, and two compounds showed sub-millimolar inhibition. These compounds are the first small molecule inhibitors of the Fem ligase family of peptidyltransferases found in Gram-positive bacteria. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.028