(3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronic acid 6′-methylester | 1185255-36-0

• 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: (3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronic acid 6′-methylester
• 英文别名: glycyrrhizic acid 6'-methyl ester；Glycyrrhizin-6'-methylester；(2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-4,5-dihydroxy-6-methoxycarbonyloxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 1185255-36-0
• 化学式: C₄₃H₆₄O₁₆
• 分子量: 836.972
• InChiKey: AOBUVNAZHQBLHP-ILVQQCHOSA-N

物化性质

• 沸点：
  934.0±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  59
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  256
• 氢给体数：
  7
• 氢受体数：
  16

制备方法与用途

glycyrrhizin-6'-methylester 是一种可以从甘草（Glycyrrhiza glabra）中分离得到的天然产物。

反应信息

• 作为产物：
  描述：

  甲醇 、 (3beta,20beta)-20-羧基-11-氧代-30-去甲齐墩果-12-烯-3-基 2-O-beta-D-吡喃葡糖基-beta-D-吡喃葡糖苷酸 在 乙酰氯 作用下， 以11%的产率得到(3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronic acid 6′-methylester
  参考文献：
  名称：

  Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems

  摘要：

  Immunostimulatory saponin based colloidal antigen delivery systems show promise as adjuvants for subunit vaccines. For this reason, allyl oleanolate was glycosylated at the 3-position using trichloroacetimidate donors to give monodesmodic saponins following deprotection. Bisdesmodic saponins were synthesized by double glycosylation at the 3- and 28-positions of oleanolic acid. When formulated together with cholesterol and phospholipids, ring-like, helical and rod-like nanostructures were formed depending on the saponin concentrations used. As an indication of adjuvant activity, the ability of these formulations, and the saponins by themselves, to induce dendritic cell maturation was measured, but no significant activity was observed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.043

文献信息

• Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems
  作者：Alison M. Daines、Ben W. Greatrex、Colin M. Hayman、Sarah M. Hook、Warren T. McBurney、Thomas Rades、Phillip M. Rendle、Ian M. Sims

  DOI：10.1016/j.bmc.2009.05.043

  日期：2009.7

  Immunostimulatory saponin based colloidal antigen delivery systems show promise as adjuvants for subunit vaccines. For this reason, allyl oleanolate was glycosylated at the 3-position using trichloroacetimidate donors to give monodesmodic saponins following deprotection. Bisdesmodic saponins were synthesized by double glycosylation at the 3- and 28-positions of oleanolic acid. When formulated together with cholesterol and phospholipids, ring-like, helical and rod-like nanostructures were formed depending on the saponin concentrations used. As an indication of adjuvant activity, the ability of these formulations, and the saponins by themselves, to induce dendritic cell maturation was measured, but no significant activity was observed. (C) 2009 Elsevier Ltd. All rights reserved.