penicillin V | 6153-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: penicillin V
• 英文别名: penicillin；6β-Phenoxyacetamido-2,2-dimethylpenam-3α-carboxylic acid；(2R,5S,6S)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS: 6153-25-9
• 化学式: C₁₆H₁₈N₂O₅S
• 分子量: 350.395
• InChiKey: BPLBGHOLXOTWMN-SCRDCRAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α-环糊精 、 penicillin V 以 甲醇 、 水 为溶剂， 生成 α-cyclodextrin-penicillin V complex
  参考文献：
  名称：

  Molecular recognition: .alpha.-cyclodextrin and penicillin V inclusion complexation

  摘要：

  Specific molecular recognition between alpha-cyclodextrin (1) and a beta-lactam antibiotic, penicillin V (2), was systematically determined. A stable 1:1 inclusion complex was established in the solid state, gaseous phase, and solution. The distinct structure of this inclusion complex was rigorously elucidated by FT-IR, FAB-MS, CP/MAS solid-state C-13 NMR, and 500-MHz H-1 NMR. Based on strictly determined H-1 NMR data, a time-averaged conformation of the alpha-CD-penicillin V inclusion complex was proposed, which was supported by CPK model studies and the intermolecular NOE results. Moreover, alpha-cyclodextrin exhibited significant catalytic activity toward the hydrolysis of penicillin V in weakly alkaline solution. These findings imply that the initial molecular recognition and the concomitant molecular association are essential in a biomimetic process.

  DOI：

  10.1021/jo00004a037
• 作为产物：
  描述：

  (R)-((2R)-4t-carboxy-5,5-dimethyl-thiazolidin-2r-yl)-(2-phenoxy-acetylamino)-acetic acid 在 1,4-二氧六环 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 生成 penicillin V
  参考文献：
  名称：

  The Total Synthesis of Penicillin V

  摘要：

  DOI：

  10.1021/ja01521a044

文献信息

• Process for the preparation of esters of N-blocked penicillin acids
  申请人：Glaxo Laboratories Limited

  公开号：US03960843A1

  公开（公告）日：1976-06-01

  A process is described for the preparation of esters of N-blocked amino acids (such as penicillins or cephalosporins) wherein the amino acid or a salt thereof is reacted with a primary amine and nitrosating agent.

  描述了一种制备N-阻滞氨基酸酯类化合物（如青霉素或头孢菌素）的方法，其中氨基酸或其盐与一种一级胺和亚硝化剂发生反应。
• The Total Synthesis of Penicillin V
  作者：John C. Sheehan、Kenneth R. Henery-Logan

  DOI：10.1021/ja01521a044

  日期：1959.6
• Molecular recognition: .alpha.-cyclodextrin and penicillin V inclusion complexation
  作者：Zhihong Helena Qi、Vivien Mak、Luis Diaz、David M. Grant、Ching Jer Chang

  DOI：10.1021/jo00004a037

  日期：1991.2

  Specific molecular recognition between alpha-cyclodextrin (1) and a beta-lactam antibiotic, penicillin V (2), was systematically determined. A stable 1:1 inclusion complex was established in the solid state, gaseous phase, and solution. The distinct structure of this inclusion complex was rigorously elucidated by FT-IR, FAB-MS, CP/MAS solid-state C-13 NMR, and 500-MHz H-1 NMR. Based on strictly determined H-1 NMR data, a time-averaged conformation of the alpha-CD-penicillin V inclusion complex was proposed, which was supported by CPK model studies and the intermolecular NOE results. Moreover, alpha-cyclodextrin exhibited significant catalytic activity toward the hydrolysis of penicillin V in weakly alkaline solution. These findings imply that the initial molecular recognition and the concomitant molecular association are essential in a biomimetic process.