benzyl (2R)-2-(((1-(((benzyloxy)carbonyl)amino)ethyl)(methoxy)phosphoryl)oxy)-3-methylbutanoate | 1356037-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (2R)-2-(((1-(((benzyloxy)carbonyl)amino)ethyl)(methoxy)phosphoryl)oxy)-3-methylbutanoate
• CAS: 1356037-48-3
• 化学式: C₂₃H₃₀NO₇P
• 分子量: 463.467
• InChiKey: PUKTXROTIFXWTP-VKXRZJHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  100.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  benzyl (2R)-2-(((1-(((benzyloxy)carbonyl)amino)ethyl)(methoxy)phosphoryl)oxy)-3-methylbutanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis, characterization and activity of new phosphonate dipeptides as potential inhibitors of VanX

  摘要：

  VanX, a Zn(II)-dependent D-ala-D-ala dipeptidase, is essential for vancomycin resistance in Enterococcus faecium. The enzymatic activity of VanX was previously found to be inhibited competitively by 2-{[(1-aminoethyl) (hydroxy) phosphoryl]oxy} propanoic acid (1B). Here we report the synthesis and characterization of seven phosphonate dipeptide analogs of D-ala-D-ala with various substituent, the activity evaluation indicated that six of these phosphonate analogs inhibit VanX with IC50 of 0.48-8.21 mM. These data revealed a structure-activity relationship which is that the large substituent group on beta-carbon resulted in low binding affinity of the phonphonate analog to VanX. This information will be helpful to guide the design and synthesis of the tightly-binding inhibitors for VanX. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.094
• 作为产物：
  描述：

  D-缬氨酸 在 硫酸 、 对甲苯磺酸 、 三乙胺 、 sodium nitrite 作用下， 以 氯仿 、 水 、 苯 为溶剂， 反应 99.5h， 生成 benzyl (2R)-2-(((1-(((benzyloxy)carbonyl)amino)ethyl)(methoxy)phosphoryl)oxy)-3-methylbutanoate
  参考文献：
  名称：

  Synthesis, characterization and activity of new phosphonate dipeptides as potential inhibitors of VanX

  摘要：

  VanX, a Zn(II)-dependent D-ala-D-ala dipeptidase, is essential for vancomycin resistance in Enterococcus faecium. The enzymatic activity of VanX was previously found to be inhibited competitively by 2-{[(1-aminoethyl) (hydroxy) phosphoryl]oxy} propanoic acid (1B). Here we report the synthesis and characterization of seven phosphonate dipeptide analogs of D-ala-D-ala with various substituent, the activity evaluation indicated that six of these phosphonate analogs inhibit VanX with IC50 of 0.48-8.21 mM. These data revealed a structure-activity relationship which is that the large substituent group on beta-carbon resulted in low binding affinity of the phonphonate analog to VanX. This information will be helpful to guide the design and synthesis of the tightly-binding inhibitors for VanX. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.094