Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(2-benzyloxycarbonylamino-acetylamino)-6-hydroxy-tetrahydro-pyran-4-yl ester | 856570-65-5

• 分子结构分类: 有机化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(2-benzyloxycarbonylamino-acetylamino)-6-hydroxy-tetrahydro-pyran-4-yl ester
• CAS: 856570-65-5
• 化学式: C₂₂H₂₈N₂O₁₁
• 分子量: 496.471
• InChiKey: VAQJXTMMOLLEBB-MLZLACJZSA-N

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(2-benzyloxycarbonylamino-acetylamino)-6-hydroxy-tetrahydro-pyran-4-yl ester 在 palladium on activated charcoal 四氮唑 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Identification of Active-Site Inhibitors of MurG Using a Generalizable, High-Throughput Glycosyltransferase Screen

  摘要：

  MurG is a glycosyltransferase involved in the biosynthesis of bacterial peptidoglycan. It is a potentially important antibiotic target, but no inhibitors of the enzyme have been reported. In general, inhibitors of glycosyltransferases have been difficult to design. Furthermore, no glycosyltransferase inhibitors have been identified through high-throughput screening, perhaps because appropriate screens for glycosyltransferase inhibition have not been developed. In this manuscript, we describe the development of a high-throughput screen for MurG that was used to screen a 50 000 compound library for inhibitors. The screen, which can be generalized to other glycosyltransferases, led to the identification of a family of active-site directed MurG inhibitors. The family of inhibitors contains a five-membered heterocyclic core that appears to function as a diphosphate mimic with respect to the presentation of substituents. We discuss the implications of this result and the utility of the screen for identifying inhibitors of other glycosyltransferases.

  DOI：

  10.1021/ja036494s
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(2-benzyloxycarbonylamino-acetylamino)-tetrahydro-pyran-4-yl ester 在 乙酸肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以87%的产率得到Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(2-benzyloxycarbonylamino-acetylamino)-6-hydroxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Identification of Active-Site Inhibitors of MurG Using a Generalizable, High-Throughput Glycosyltransferase Screen

  摘要：

  MurG is a glycosyltransferase involved in the biosynthesis of bacterial peptidoglycan. It is a potentially important antibiotic target, but no inhibitors of the enzyme have been reported. In general, inhibitors of glycosyltransferases have been difficult to design. Furthermore, no glycosyltransferase inhibitors have been identified through high-throughput screening, perhaps because appropriate screens for glycosyltransferase inhibition have not been developed. In this manuscript, we describe the development of a high-throughput screen for MurG that was used to screen a 50 000 compound library for inhibitors. The screen, which can be generalized to other glycosyltransferases, led to the identification of a family of active-site directed MurG inhibitors. The family of inhibitors contains a five-membered heterocyclic core that appears to function as a diphosphate mimic with respect to the presentation of substituents. We discuss the implications of this result and the utility of the screen for identifying inhibitors of other glycosyltransferases.

  DOI：

  10.1021/ja036494s