(-)-menthol α-D-glucoside | 67462-22-0

• 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: (-)-menthol α-D-glucoside
• 英文别名: ((1R)-menthyl)-α-D-glucopyranoside；((1R)-Menthyl)-α-D-glucopyranosid；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxyoxane-3,4,5-triol
• CAS: 67462-22-0
• 化学式: C₁₆H₃₀O₆
• 分子量: 318.411
• InChiKey: GZSDZJZIZBGBON-HQUOFDGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-menthol α-D-glucoside 在 吡啶 、 alkaline aqueous sodium hypobromite solution 作用下， 生成 O¹-((1R)-menthyl)-α-D-glucopyranuronic acid
  参考文献：
  名称：

  Bergmann; Wolff, Chemische Berichte, 1923, vol. 56, p. 1060,1064

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖酰氟 在 三氟化硼乙醚 、 potassium carbonate 、 四甲基胍 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成 (-)-menthol α-D-glucoside
  参考文献：
  名称：

  Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases

  摘要：

  Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C roseus enantioselectively glucosylated (+/-)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.022

文献信息

• Anomer-Selective Glucosylation of<i>l</i>-Menthol by Yeast α-Glucosidase
  作者：Hiroyuki NAKAGAWA、Masaaki YOSHIYAMA、Susumu SHIMURA、Kohtaro KIRIMURA、Shoji USAMI

  DOI：10.1271/bbb.62.1332

  日期：1998.1

  l-Menthol was glucosylated by the α-glucosidase (EC 3.2.1.20) of Saccharomyces cerevisiae using maltose as the glucosyl donor. When 50 mg of l-menthol and 1.6 M maltose in 10 mM citrate-phosphate buffer (pH 5.5) were incubated at 45°C, l-menthyl α-D-glucopyranoside (α-MenG) was α-anomer-selectively formed as a product. The specificity of the α-linkage was confirmed by 13C-NMR analysis. In the reaction mixture after 2 h, α-MenG was mainly accumulated in a crystalline form and the concentration of dissolved α-MenG was constant at 1.4 mM. The molar conversion yield of α-MenG produced based on the supplied l-menthol was maximally 30.7% at 48 h of reaction.

  以麦芽糖为葡萄糖基供体，通过酿酒酵母的α-葡萄糖苷酶（EC 3.2.1.20）对薄荷醇进行葡萄糖基化。在 10 mM 柠檬酸盐-磷酸盐缓冲液（pH 5.5）中加入 50 mg l-menthol 和 1.6 M 麦芽糖，在 45°C 下孵育，l-menthyl α-D-glucopyranoside (α-MenG)作为一种产物选择性地形成了 α-异构体。13C-NMR 分析证实了 α 连接的特异性。2 小时后，α-MenG 在反应混合物中主要以结晶形式积累，溶解的 α-MenG 浓度保持在 1.4 mM。在反应 48 小时后，以提供的 l-薄荷醇为基础生成的 α-MenG摩尔转化率最高为 30.7%。
• Anomer Selective Formation of<i>l</i>-Menthyl<i>α</i>-<scp>D</scp>-Glucopyranoside by<i>α</i>-Glucosidase-catalyzed Reaction
  作者：Hiroyuki Nakagawa、Masaaki Yoshiyama、Susumu Shimura、Kohtaro Kirimura、Shoji Usami

  DOI：10.1271/bbb.60.1914

  日期：1996.1

  l-Menthol was glucosylated by the α-glucosidase (EC 3.2.1.20) of Saccharomyces cerevisiae using maltose as glucosyl donor. When 50 mg of l-menthol and 1M maltose in 10 mM citrate–phosphate buffer (pH 7.0) were incubated for 24 h at 30°C, a menthylglucoside was selectively obtained as a product. The molar conversion yield based on supplied menthol was 4.5%. The product was identified as l-menthyl α-D-glucopyranoside (α-MenG) by 13C-NMR analysis.

  l-薄荷醇通过酿酒酵母的α-葡萄糖苷酶（EC 3.2.1.20）进行葡萄糖基化，以麦芽糖作为葡萄糖基供体。当50 mg l-薄荷醇和1M麦芽糖在10 mM柠檬酸-磷酸盐缓冲液（pH 7.0）中于30°C下孵育24小时时，选择性获得薄荷醇葡萄糖苷作为产物。基于提供的薄荷醇的摩尔转化率为4.5%。通过13C-NMR分析，该产品被鉴定为l-薄荷醇α-D-吡喃葡萄糖苷（α-MenG）。
• Neuberg et al., Fermentforschung, 1929, vol. 10, p. 491,515, 516, 520
  作者：Neuberg et al.

  DOI：——

  日期：——
• 289. The synthesis of conjugated hexuronic acids
  作者：C. A. Marsh

  DOI：10.1039/jr9520001578

  日期：——
• Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases
  作者：Kei Shimoda、Naoji Kubota、Hiroki Hamada

  DOI：10.1016/j.tetasy.2004.06.022

  日期：2004.8

  Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C roseus enantioselectively glucosylated (+/-)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols. (C) 2004 Elsevier Ltd. All rights reserved.