<(5Z,7E)-(3S)-3-hydroxy-9,10-secocholesta-5,7,10(19)-trien-25-yl>-β-D-glucopyranosiduronic acid

• 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: <(5Z,7E)-(3S)-3-hydroxy-9,10-secocholesta-5,7,10(19)-trien-25-yl>-β-D-glucopyranosiduronic acid
• 英文别名: 25-hydroxyvitamin D₃ 25-monoglucuronide；25-hydroxyvitamin D₃ 25-glucuronide；25(OH)D₃25G；(6R)-6-[(1R,3aS,4E,7aR)-4-{(2Z)-2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyloctahydro-1H-inden-1-yl]-2-methylheptan-2-yl beta-D-glucopyranosiduronic acid；(2S,3S,4S,5R,6S)-6-[(6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-methylheptan-2-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₃₃H₅₂O₈
• 分子量: 576.771
• InChiKey: RQQPJTROOXJOLQ-IBWLQHGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl(cholesta-5,7-dien-3β-ol-25-yl-2',3',4'-tri-O-acetyl-β-D-glucopyranosid)uronate 在 氢氧化钾 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 <(5Z,7E)-(3S)-3-hydroxy-9,10-secocholesta-5,7,10(19)-trien-25-yl>-β-D-glucopyranosiduronic acid
  参考文献：
  名称：

  Syntheses and Enzymatic Hydrolysis of 25-Hydroxyvitamin D Monoglucuronides.

  摘要：

  以相应的维生素 D 或其衍生物为原料，以碳酸银为催化剂，通过柯尼希斯-克诺尔反应合成 25-羟基维生素 D3（D2）3-和 25-单葡糖苷酸，然后进行光化学反应、热异构化和碱水解。使用 β-葡萄糖醛酸酶对获得的葡萄糖醛酸进行酶水解，发现所研究的酶具有不同来源的底物特异性。

  DOI：

  10.1248/cpb.43.1379

文献信息

• In Vitro Glucuronidation of 25-Hydroxyvitamin D3 and Its Pro-form.
  作者：Kazutake SHIMADA、Yuko KAMEZAWA、Kuniko MITAMURA

  DOI：10.1248/bpb.20.596

  日期：——

  In vitro glucuronidation of 25-hydroxyvitamin D3 and its pro-form has been investigated by means of HPLC with UV detection. Although both substrates gave 3- and 25-glucuronides in the presence of the ray liver microsomal fraction and uridine-5'-diphosphoglucuronic acid, 25-hydroxyvitamin D3 and its pro-form yielded 3- and 25-glucuronide as the main product, respectively. The latter glucuronide is the one in which the tert-hydroxy group is conjugated. Each glucuronide was identified by its chromatographic behavior in comparison with an authentic sample and data obtained from liquid chromatography/mass spectrometry (LC/MS) using atmospheric pressure chemical ionization.

  通过高效液相色谱法和紫外检测法对 25-羟基维生素 D3 及其原形的体外葡萄糖醛酸化进行了研究。虽然这两种底物在鳐鱼肝微粒体组分和尿苷-5'-二磷酸葡萄糖醛酸的存在下都会产生 3-和 25-葡萄糖醛酸，但 25-羟基维生素 D3 及其原形的主要产物分别是 3-和 25-葡萄糖醛酸。后一种葡萄糖醛酸是与叔羟基共轭的葡萄糖醛酸。每种葡萄糖醛酸苷都是通过其色谱行为与真实样品和使用常压化学电离的液相色谱/质谱法（LC/MS）获得的数据进行比较而确定的。
• Syntheses and Enzymatic Hydrolysis of 25-Hydroxyvitamin D Monoglucuronides.
  作者：Kazutake SHIMADA、Katsuko SUGAYA、Hidefumi KAJI、ITO NAKATANI、Kuniko MITAMURA、Noriko TSUTSUMI

  DOI：10.1248/cpb.43.1379

  日期：——

  25-Hydroxyvitamin D3 (D2) 3- and 25-monoglucuronides were synthesized from the corresponding provitamin D or its derivatives with the Koenigs-Knorr reaction using silver carbonate as a catalyst, followed by photochemical reaction, thermal isomerization and then alkali hydrolysis. The obtained glucuronides were subjected to enzymatic hydrolysis using β-glucuronidase, and substrate specificities were found in the examined enzymes originating from different sources.

  以相应的维生素 D 或其衍生物为原料，以碳酸银为催化剂，通过柯尼希斯-克诺尔反应合成 25-羟基维生素 D3（D2）3-和 25-单葡糖苷酸，然后进行光化学反应、热异构化和碱水解。使用 β-葡萄糖醛酸酶对获得的葡萄糖醛酸进行酶水解，发现所研究的酶具有不同来源的底物特异性。