<2-13C,3-2H>penicillin N | 148225-10-9

• 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: <2-13C,3-2H>penicillin N
• 英文别名: (2S,5R,6R)-6-[[(5R)-5-amino-5-carboxypentanoyl]amino]-2-deuterio-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS: 148225-10-9
• 化学式: C₁₄H₂₁N₃O₆S
• 分子量: 361.384
• InChiKey: MIFYHUACUWQUKT-YPSWHKEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  175
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  <2-13C,3-2H>penicillin N 在 deacetoxy 、 deacetylcephalosporin C synthase dioxygen-(16)O 、 2-氧代-戊二酸离子(2-) 作用下， 以 水 为溶剂， 反应 2.0h， 以0.174 mg的产率得到<3-13C>deacetoxycephalosporin C
  参考文献：
  名称：

  Incorporation of 18O-labelled water into oxygenated products produced by the enzyme deacetoxy/deacetylcephalosporin C synthase

  摘要：

  O-18-labelling experiments have been conducted with the enzyme deacetoxy/deacetylcephalosporin C synthase. Incubations of [2-C-13,3-H-2]penicillin N and [4-H-2]exomethylene cephalosporin C were carried out with O-18(2) or (H2O)-O-18, and O-18-incorporation from both label sources was observed into the oxygenated enzymic products. This is believed to be the first example of (H2O)-incorporation into products of an alpha-ketoglutarate dependent dioxygenase. An oxygen-exchange process at an enzyme-bound intermediate is proposed to account for this incorporation.

  DOI：

  10.1016/s0040-4020(01)87226-4
• 作为产物：
  描述：

  [(5R)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-(2-²H,3-¹³C)-valine trifluoroacetate 在 L-ascorbate 、 isopenicillin N synthetase enzyme 、 氧气 、 iron(II) sulfate 、 Cleland's reagent 作用下， 以 various solvent(s) 为溶剂， 反应 0.67h， 以2.8 mg的产率得到<2-13C,3-2H>penicillin N
  参考文献：
  名称：

  The enzymatic synthesis of isotopically labelled penicillin Ns with isopenicillin N synthase

  摘要：

  DOI：

  10.1002/(sici)1099-1344(199812)41:12<1145::aid-jlcr159>3.0.co;2-2

文献信息

• Water exchange of intermediates in a non-haem iron, α-ketoglutarate dioxygenase, deacetoxy-/deacetylcephalosporin C synthase
  作者：Jack E. Baldwin、Robert M. Adlington、Nicholas P. Crouch、Inês A. C. Pereira、Robin T. Aplin、Carol Robinson

  DOI：10.1039/c39930000105

  日期：——

  Incubation of [2-13C, 3-2H]penicillin N 1c and [4-2H]exomethylene cephalosporin C 5b with the enzyme deacetoxy-/deacetylcephalosporin C synthase (DAOC/DAC synthase) in 18O-labelled water gave oxygenated products showing significant incorporation of 18O; the observed levels of incorporation from 18O-labelled water are complementary to the previously reported incorporations which were achieved from molecular oxygen, and we believe this to be a first example of H218O incorporation into enzymic products catalysed by a non-haem iron, α-ketoglutarate dependent dioxygenase, and suggest structures for the exchanging intermediates.