3β-acetoxy-ergosta-5,7,22t,24(28)-tetraene | 31664-30-9

• 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: 3β-acetoxy-ergosta-5,7,22t,24(28)-tetraene
• 英文别名: 3β-Acetoxy-ergosta-5,7,22t,24(28)-tetraen；Ergosta-5,7,22,24(28)-tetraen-3beta-yl acetate；[(3S,9S,10R,13R,14R,17R)-10,13-dimethyl-17-[(E,2R)-6-methyl-5-methylidenehept-3-en-2-yl]-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 31664-30-9
• 化学式: C₃₀H₄₄O₂
• 分子量: 436.678
• InChiKey: BHQJNSKSHBXZQJ-UUIIXSECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-ergosta-5,7,22t,24(28)-tetraene 、 水 生成 乙酸盐 、 24(28)-去氢麦角甾醇 、 氢(+1)阳离子
  参考文献：
  名称：

  An acetylation/deacetylation cycle controls the export of sterols and steroids from S. cerevisiae

  摘要：

  Sterol homeostasis in eukaryotic cells relies on the reciprocal interconversion of free sterols and steryl esters. Here we report the identification of a novel reversible sterol modification in yeast, the sterol acetylation/deacetylation cycle. Sterol acetylation requires the acetyltransferase ATF2, whereas deacetylation requires SAY1, a membrane-anchored deacetylase with a putative active site in the ER lumen. Lack of SAY1 results in the secretion of acetylated sterols into the culture medium, indicating that the substrate specificity of SAY1 determines whether acetylated sterols are secreted from the cells or whether they are deacetylated and retained. Consistent with this proposition, we find that acetylation and export of the steroid hormone precursor pregnenolone depends on its acetylation by ATF2, but is independent of SAY1-mediated deacetylation. Cells lacking Say1 or Atf2 are sensitive against the plant-derived allylbenzene eugenol and both Say1 and Atf2 affect pregnenolone toxicity, indicating that lipid acetylation acts as a detoxification pathway. The fact that homologues of SAY1 are present in the mammalian genome and functionally substitute for SAY1 in yeast indicates that part of this pathway has been evolutionarily conserved.

  DOI：

  10.1038/sj.emboj.7601924
• 作为产物：
  描述：

  24(28)-去氢麦角甾醇 、 乙酸酐 在 吡啶 作用下， 生成 3β-acetoxy-ergosta-5,7,22t,24(28)-tetraene
  参考文献：
  名称：

  A NEW TETRAETHENOID STEROL OF YEAST

  摘要：

  DOI：

  10.1021/jo01376a003

文献信息

• A NEW TETRAETHENOID STEROL OF YEAST
  作者：O. N. BREIVIK、J. L. OWADES、R. F. LIGHT

  DOI：10.1021/jo01376a003

  日期：1954.11
• An acetylation/deacetylation cycle controls the export of sterols and steroids from S. cerevisiae
  作者：Rashi Tiwari、René Köffel、Roger Schneiter

  DOI：10.1038/sj.emboj.7601924

  日期：2007.12.12

  Sterol homeostasis in eukaryotic cells relies on the reciprocal interconversion of free sterols and steryl esters. Here we report the identification of a novel reversible sterol modification in yeast, the sterol acetylation/deacetylation cycle. Sterol acetylation requires the acetyltransferase ATF2, whereas deacetylation requires SAY1, a membrane-anchored deacetylase with a putative active site in the ER lumen. Lack of SAY1 results in the secretion of acetylated sterols into the culture medium, indicating that the substrate specificity of SAY1 determines whether acetylated sterols are secreted from the cells or whether they are deacetylated and retained. Consistent with this proposition, we find that acetylation and export of the steroid hormone precursor pregnenolone depends on its acetylation by ATF2, but is independent of SAY1-mediated deacetylation. Cells lacking Say1 or Atf2 are sensitive against the plant-derived allylbenzene eugenol and both Say1 and Atf2 affect pregnenolone toxicity, indicating that lipid acetylation acts as a detoxification pathway. The fact that homologues of SAY1 are present in the mammalian genome and functionally substitute for SAY1 in yeast indicates that part of this pathway has been evolutionarily conserved.