23-deuterio-4α-methylergost-23(E)-en-3β-ol | 132591-85-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 23-deuterio-4α-methylergost-23(E)-en-3β-ol
• CAS: 132591-85-6
• 化学式: C₂₉H₅₀O
• 分子量: 415.707
• InChiKey: KWLPSAZUNJBGKE-NTXYLDIXSA-N

反应信息

• 作为产物：
  描述：

  (24R)-3β-acetoxy-4α-methylergostan-23-one 生成 (24R)-23-deuterio-4α-methylergost-22-en-3β-ol 、 23-deuterio-4α-methylergost-23(Z)-en-3β-ol 、 23-deuterio-4α-methylergost-23(E)-en-3β-ol
  参考文献：
  名称：

  Biosynthetic studies of marine lipids. 33. Biosynthesis of dinosterol, peridinosterol and gorgosterol: unusual patterns of bioalkylation in dinoflagellate sterols

  摘要：

  The biosynthesis of the 23-methylated dinoflagellate sterols gorgosterol (1-N), dinosterol (2-K), and peridinosterol (3-K) was demonstrated experimentally using cell-free extracts of the dinoflagellates Cryptothecodinium cohnii, Peridinium foliaceum, and the cultured zooxanthella symbiont of Cassiopea xamachana. In assays of sterol methyltransferases using [H-3]-S-adenosylmethionine, radiochemical conversions were demonstrated by reverse phase HPLC of the DELTA-24 sterol side chain (5) to the 24-methylene side chain (4); of the sequence 24(R)-4-alpha-methylergost-22-enol (9-K) to dinosterol (2-K) to 4-alpha-methylgorgostanol (1-K); and, in P. foliaceum, of 24-(R)-4-alpha-methylergost-22-enol (9-K) to peridinosterol (3-K). Methylation of the 24(R)-methyl DELTA-22 side chain (9) in P. foliaceum is believed to involve more than one SAM-sterol methyltransferase based on changes in the ratios of the products (2 and 3) with changes in the conditions of the assay. Furthermore, deuterium substitution of the sterol substrate (9-K) at C-23 did not significantly alter the product ratio. A hypothesis is put forward that the attenuation of gorgosterol (1-N) production in aposymbiotic zooxanthellae is linked to an increase in dimethylpropiothetin biosynthesis via a decrease in S-adenosylmethionine concentration.

  DOI：

  10.1021/jo00007a021