2-(Methyl-d3)-3-[(2E,10E)-3,7,11,15-tetramethyl-2,10,14-hexadecatrien-1-yl]-1,4-naphthalenedione-5,6,7,8-d4 | 1233937-35-3

• 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: 2-(Methyl-d3)-3-[(2E,10E)-3,7,11,15-tetramethyl-2,10,14-hexadecatrien-1-yl]-1,4-naphthalenedione-5,6,7,8-d4
• 英文别名: 5,6,7,8-tetradeuterio-2-[(2E,10E)-3,7,11,15-tetramethylhexadeca-2,10,14-trienyl]-3-(trideuteriomethyl)naphthalene-1,4-dione
• CAS: 1233937-35-3
• 化学式: C₃₁H₄₂O₂
• 分子量: 453.618
• InChiKey: JVDWWROPKLAPGD-VWDNUEOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  2-Methyl-1,4-naphthalenediol-d8 、 (2E,10E)-3,7,11,15-tetramethylhexadeca-2,10,14-trien-1-ol 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 3.0h， 以54 mg的产率得到2-(Methyl-d3)-3-[(2E,10E)-3,7,11,15-tetramethyl-2,10,14-hexadecatrien-1-yl]-1,4-naphthalenedione-5,6,7,8-d4
  参考文献：
  名称：

  Structure–activity relationships in the conversion of vitamin K analogues into menaquinone-4. Substrates essential to the synthesis of menaquinone-4 in cultured human cell lines

  摘要：

  To reveal an essential biological role of menaquinone-4, we have clarified that dietary PK was converted to menaquinone-4 (MK-4) in animal tissues using deuterated vitamin K analogues. However, the kinds of analogue converted into MK-4 have not been elucidated. In this study, we examined structure-activity relationships in the conversion of several vitamin K analogues, with a substituted side chain, into MK-4 using cultured human cell lines. The results differed with the side chain of the analogues, that is, (1) the length of the isoprene unit and (2) the number of double bonds in the side chain. These findings would be useful for clarifying the mechanism of conversion of other vitamin K homologs into MK-4 as well as related enzymes. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.035

文献信息

• Structure–activity relationships in the conversion of vitamin K analogues into menaquinone-4. Substrates essential to the synthesis of menaquinone-4 in cultured human cell lines
  作者：Yoshitomo Suhara、Akimori Wada、Yoji Tachibana、Masato Watanabe、Kanae Nakamura、Kimie Nakagawa、Toshio Okano

  DOI：10.1016/j.bmc.2010.03.035

  日期：2010.5

  To reveal an essential biological role of menaquinone-4, we have clarified that dietary PK was converted to menaquinone-4 (MK-4) in animal tissues using deuterated vitamin K analogues. However, the kinds of analogue converted into MK-4 have not been elucidated. In this study, we examined structure-activity relationships in the conversion of several vitamin K analogues, with a substituted side chain, into MK-4 using cultured human cell lines. The results differed with the side chain of the analogues, that is, (1) the length of the isoprene unit and (2) the number of double bonds in the side chain. These findings would be useful for clarifying the mechanism of conversion of other vitamin K homologs into MK-4 as well as related enzymes. (c) 2010 Elsevier Ltd. All rights reserved.