12β-hydroxycoroglaucigenin | 139562-79-1

• 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: 12β-hydroxycoroglaucigenin
• 英文别名: 12beta-Hydroxycoroglaucigenin；3-[(3S,5S,8R,9S,10R,12R,13S,14S,17R)-3,12,14-trihydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• CAS: 139562-79-1
• 化学式: C₂₃H₃₄O₆
• 分子量: 406.519
• InChiKey: HTBPPXIZDUWCFX-HGSYIYTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 12β-hydroxycoroglaucigenin 在 UGT₇₄AN₁ 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  UGT74AN1, a Permissive Glycosyltransferase from Asclepias curassavica for the Regiospecific Steroid 3-O-Glycosylation

  摘要：

  A permissive steroid glycosyltransferase (UGT74AN1) from Asclepias curassavica exhibited robust capabilities for the regiospecific C3 glycosylation of cardiotonic steroids and C-21 steroid precursors, and unprecedented promiscuity toward 53 structurally diverse natural and unnatural compounds to form O-, N-, and S-glycosides, along with the catalytic reversibility for a one-pot transglycosylation reaction. These findings highlight UGT74AN1 as the first regiospecific catalyst for cardiotonic steroid C3 glycosylation and exhibit significant potential for glycosylation of diverse bioactive molecules in drug discovery.

  DOI：

  10.1021/acs.orglett.7b03619

文献信息

• 3'-epi-19-Norafroside and 12.BETA.-Hydroxycoroglaucigenin from Asclepias curassavica.
  作者：Fumiko ABE、Yujiro MORI、Tatsuo YAMAUCHI

  DOI：10.1248/cpb.39.2709

  日期：——

  3'-epi-19-Norafraside, a 19-norcardenolide glycoside with dual linkages between a cardenolide and 4, 6-dideoxy-galactos-2-ulose, and 12β-hydroxycoroglausigenin were newly isolated from the stems of Asclepias curassavica, along with known glycosides and free cardenolides. The structures were determined by spectral and chemical methods.

  3'-表-19-去甲阿福花苷是一种19-去甲阿福花甾醇苷，在阿福花甾醇和4,6-二脱氧半乳糖-2-酮之间具有双重连接，12β-羟基科罗格劳辛素是从库拉索芦荟的茎中分离出来的，还有已知的苷类和游离阿福花甾醇。通过光谱和化学方法确定了结构。