vitamin K-1-18O

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: vitamin K-1-18O
• 英文别名: 2-methyl-3-[(E)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-di(18O)one
• 化学式: C₃₁H₄₆O₂
• 分子量: 452.706
• InChiKey: MBWXNTAXLNYFJB-FAKCLFGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-Methoxy-3-methyl-2-(3,7,11,15-tetramethyl-2-hexadecenyl)-1-naphthol 在 ammonium cerium(IV) nitrate 、 重氧水 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以10.4 mg的产率得到vitamin K-1-18O
  参考文献：
  名称：

  [1-18O] 和 [4-18O] 维生素 K1 的简便合成

  摘要：

  Na 2 S 2 O 4 将维生素 K 1 定量还原为二氢维生素 K 1 (2)。氢醌2被CH 3 I/K 2 CO 3 部分甲基化，得到1和4单甲醚的混合物，其通过HPLC分离。在[ 18 O] H 2 O 存在下，每种单醚都被硝酸铈铵氧化，以提供同位素富集为93-95% 的特定标记的[1- 18 O] 或[4- 18 O] 维生素K 1。

  DOI：

  10.1002/(sici)1099-1344(199802)41:2<115::aid-jlcr58>3.0.co;2-8

文献信息

• Active site of vitamin K. Regiospecific oxygenation of vitamin K hydroquinone in its role as carboxylase cofactor
  作者：Sriram Naganathan、Roger Hershline、Seung Wook Ham、Paul Dowd

  DOI：10.1021/ja00066a068

  日期：1993.6
• The Active Site of Vitamin K and the Role of the Vitamin K-Dependent Carboxylase
  作者：Sriram Naganathan、Roger Hershline、Seung Wook Ham、Paul Dowd

  DOI：10.1021/ja00101a003

  日期：1994.11

  Vitamin K is the blood-clotting vitamin. It participates in the blood coagulation cascade as a carboxylase cofactor. Enzymic oxygenation of vitamin K hydroquinone provides the driving force for the carboxylation of selected glutamates in the proteins of the blood-clotting cascade. The active site of vitamin K has now been defined by O-18-labeling experiments. The oxygenation is completely specific for the carbonyl group adjacent to the quinone methyl group of vitamin K. The experiment makes use of the O-18-labeled vitamin K isotopomers 9 and 10. Thus, oxygenation of 9 with O-16(2) occurs at the carbonyl group next to methyl, as shown by exchange of the O-18 label at that position. Synthesis of the two O-18-labeled vitamin K isotopomers 9 and 10 was accomplished by cerium(IV)-mediated oxidation in the presence of (H2O)-O-18 of the corresponding methyl half-ethers 4 and 8. The position of the label was ascertained by C-13 and heteronuclear NOE NMR spectroscopies. A role for the active site thiols on the vitamin K-dependent carboxylase is also suggested. The thiolate anion is an excellent candidate for the weak base that initiates the base strength amplification sequence leading to carboxylation and vitamin K oxide formation.