benzyl (2S,5R,6R)-3,3,6-trimethyl-6-[[(5R)-6-[(4-nitrophenyl)methoxy]-5-[(4-nitrophenyl)methoxycarbonylamino]-6-oxohexanoyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | 388568-32-9

• 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: benzyl (2S,5R,6R)-3,3,6-trimethyl-6-[[(5R)-6-[(4-nitrophenyl)methoxy]-5-[(4-nitrophenyl)methoxycarbonylamino]-6-oxohexanoyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 388568-32-9
• 化学式: C₃₇H₃₉N₅O₁₂S
• 分子量: 777.809
• InChiKey: PZUAXNSEHUIJBO-QUOXMYOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  55
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  257
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  benzyl (2S,5R,6R)-3,3,6-trimethyl-6-[[(5R)-6-[(4-nitrophenyl)methoxy]-5-[(4-nitrophenyl)methoxycarbonylamino]-6-oxohexanoyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 在 palladium on activated charcoal deacetoxy 、 deacetoxycephalosporin C synthase 、 deacetylcephalosporin C synthase 、 氢气 、 铁粉 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 (2R)-2-[(2R)-1-amino-2-[[(5R)-5-amino-5-carboxypentanoyl]amino]-1-oxopropan-2-yl]-5-formyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
  参考文献：
  名称：

  Contrasting fates for 6-α-methylpenicillin N upon oxidation by deacetoxycephalosporin C synthase (DAOCS) and deacetoxy/deacetylcephalosporin C synthase (DAOC/DACS)

  摘要：

  6-alpha -Methylpenicillin N was synthesised via known routes from 6-aminopenicillanic acid, and tested as a substrate for recombinant DAOCS and DAOC/DACS. Incubation with DAOCS resulted in conversion of 2-oxoglutarate without oxidation of the penicillin substrate ('uncoupled turnover'). Incubation with DAOC/DACS resulted in oxidation to the cephem aldehyde. This is the first example of substrate-induced 'uncoupled turnover', which has been proposed to be an editing mechanism for these enzymes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00470-x
• 作为产物：
  描述：

  6-氨基青霉烷酸 在 N-氯-N-吡啶基乙酰肼 、 magnesium sulfate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 对甲苯磺酸 、 苯基锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 98.5h， 生成 benzyl (2S,5R,6R)-3,3,6-trimethyl-6-[[(5R)-6-[(4-nitrophenyl)methoxy]-5-[(4-nitrophenyl)methoxycarbonylamino]-6-oxohexanoyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  Contrasting fates for 6-α-methylpenicillin N upon oxidation by deacetoxycephalosporin C synthase (DAOCS) and deacetoxy/deacetylcephalosporin C synthase (DAOC/DACS)

  摘要：

  6-alpha -Methylpenicillin N was synthesised via known routes from 6-aminopenicillanic acid, and tested as a substrate for recombinant DAOCS and DAOC/DACS. Incubation with DAOCS resulted in conversion of 2-oxoglutarate without oxidation of the penicillin substrate ('uncoupled turnover'). Incubation with DAOC/DACS resulted in oxidation to the cephem aldehyde. This is the first example of substrate-induced 'uncoupled turnover', which has been proposed to be an editing mechanism for these enzymes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00470-x

文献信息

• Contrasting fates for 6-α-methylpenicillin N upon oxidation by deacetoxycephalosporin C synthase (DAOCS) and deacetoxy/deacetylcephalosporin C synthase (DAOC/DACS)
  作者：Christopher S Hamilton、Akito Yasuhara、Jack E Baldwin、Matthew D Lloyd、Peter J Rutledge

  DOI：10.1016/s0960-894x(01)00470-x

  日期：2001.9

  6-alpha -Methylpenicillin N was synthesised via known routes from 6-aminopenicillanic acid, and tested as a substrate for recombinant DAOCS and DAOC/DACS. Incubation with DAOCS resulted in conversion of 2-oxoglutarate without oxidation of the penicillin substrate ('uncoupled turnover'). Incubation with DAOC/DACS resulted in oxidation to the cephem aldehyde. This is the first example of substrate-induced 'uncoupled turnover', which has been proposed to be an editing mechanism for these enzymes. (C) 2001 Elsevier Science Ltd. All rights reserved.