(-)-menthyl β-D-glucopyranoside | 16203-27-3

• 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: (-)-menthyl β-D-glucopyranoside
• 英文别名: (-)-Menthyl O-beta-D-glucoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxyoxane-3,4,5-triol
• CAS: 16203-27-3
• 化学式: C₁₆H₃₀O₆
• 分子量: 318.411
• InChiKey: GZSDZJZIZBGBON-NZZARTGWSA-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：

  (-)-menthyl β-D-glucopyranoside 在 phosphate buffer 、 almond-β-glucosidase 作用下， 反应 24.0h， 生成 L-薄荷醇
  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
• 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 (-)-menthyl β-D-glucopyranoside
  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

• Inhibitory Effect of Perillosides A and C, and Related Monoterpene Glucosides on Aldose Reductase and Their Structure-Activity Relationships.
  作者：Tomoyuki FUJITA、Kumiko OHIRA、Kazutaka MIYATAKE、Yoshihisa NAKANO、Mitsuru NAKAYAMA

  DOI：10.1248/cpb.43.920

  日期：——

  Monoterpene glucosides, perillosides A and C, obtained from the leaves of Perilla frutescens, were found to be inhibitors of aldose reductase (EC 1.1.1.21) which is considered to be a key enzyme in diabetic complications such as cataract. The apparent type of inhibition of rat lens aldose reductase by perillosides A and C was competitive with respect to glyceraldehyde and their Ki values were 1.4×10-4 and 2.3×10-4M, respectively. The type of inhibition by their tetraacetates was non-competitive with respect to the same substrate, although their inhibitory effects were increased by about one order of magnitude compared with those of the perillosides and the Ki values were 2.5×10-5 and 7.1×10-5M, respectively. We also prepared related monoterpene glucosides and their tetraacetates and determined their inhibitory activities towards aldose reductase in order to elucidate the relationship between structure and inhibitory activity.

  从紫苏（Perilla frutescens）叶中获得的单萜葡萄糖苷，紫苏苷A和C，被发现是醛糖还原酶（EC 1.1.1.21）的抑制剂，该酶被认为是糖尿病并发症如白内障的关键酶。紫苏苷A和C对大鼠晶状体醛糖还原酶的抑制作用相对于甘油醛是竞争性的，其Ki值分别为1.4×10-4和2.3×10-4M。它们的四乙酸酯对同一底物的抑制类型是非竞争性的，尽管其抑制效果比紫苏苷提高了大约一个数量级，Ki值分别为2.5×10-5和7.1×10-5M。我们还制备了相关的单萜葡萄糖苷及其四乙酸酯，并测定了它们对醛糖还原酶的抑制活性，以便阐明结构与抑制活性之间的关系。
• Remote Electronic Effects by Ether Protecting Groups Fine-Tune Glycosyl Donor Reactivity
  作者：Mads Heuckendorff、Lulu Teressa Poulsen、Henrik H. Jensen

  DOI：10.1021/acs.joc.6b00528

  日期：2016.6.17

  para-substituted benzyl ether protecting groups affect the reactivity of glycosyl donors of the thioglycoside type with the N-iodosuccinimide/triflic acid promoter system. Having electron donating p-methoxy-benzyl ether (PMB) groups increased the reactivity of the donor in comparison to having electron withdrawing p-chloro (PClB) or p-cyanobenzyl ether (PCNB) protecting groups, which decreased the reactivity

  已经确定，对位取代的苄基醚保护基团影响硫代糖苷类型的糖基供体与N-碘琥珀酰亚胺/三氟乙酸促进剂系统的反应性。与具有吸电子对氯基（PClB）或对氰基苄基醚（PCNB）保护基相比，具有给电子的对甲氧基苄基醚（PMB）基增加了供体的反应性，从而降低了糖基给体的反应性相对于母体苄基醚（Bn）保护的糖基供体。这些发现被用于通过调节它们的反应性而在两个苄基化的葡萄糖基供体之间进行第一次武装-解除武装的偶联。另外，本发明描述了高效的钯催化的对氯苄基保护的硫代糖苷的多重氰化和甲氧基化。
• Improvement of the pharmacological activity of menthol via enzymatic β-anomer-selective glycosylation
  作者：Ha-Young Choi、Bo-Min Kim、Abubaker M. A. Morgan、Joong Su Kim、Won-Gon Kim

  DOI：10.1186/s13568-017-0468-0

  日期：2017.12

  Menthol has a considerable cooling effect, but the use range of menthol is limited because of its extremely low solubility in water and inherent flavor. (−)-Menthol β-glucoside was determined to be more soluble in water (>27 times) than (−)-menthol α-glucoside; hence, β-anomer-selective glucosylation of menthol is necessary. The in vitro glycosylation of (−)-menthol by uridine diphosphate glycosyltransferase (BLC) from Bacillus licheniformis generated (−)-menthol β-glucoside and new (−)-menthol β-galactoside and (−)-menthol N-acetylglucosamine. The maximum conversion rate of menthol to (−)-menthol β-d-glucoside by BLC was found to be 58.9%. Importantly, (−)-menthol β-d-glucoside had a higher cooling effect and no flavor compared with menthol. In addition, (−)-menthol β-d-glucoside was determined to be a non-sensitizer in a skin allergy test in the human cell line activation test, whereas menthol was a sensitizer.

  薄荷醇具有显著的降温效果，但由于其在水中的溶解度极低和固有的味道，薄荷醇的使用范围受到了限制。(经测定，(-)-薄荷醇β-葡萄糖苷比(-)-薄荷醇α-葡萄糖苷更易溶于水（>27 倍）；因此，有必要对薄荷醇进行β-异构体选择性糖基化。地衣芽孢杆菌的二磷酸尿苷糖基转移酶（BLC）对（-）-薄荷醇进行体外糖基化，生成了（-）-薄荷醇β-葡萄糖苷以及新的（-）-薄荷醇β-半乳糖苷和（-）-薄荷醇N-乙酰葡萄糖胺。发现 BLC 将薄荷醇转化为(-)-薄荷醇 β-d-葡萄糖苷的最大转化率为 58.9%。重要的是，与薄荷醇相比，(-)-薄荷醇 β-d-葡萄糖苷具有更高的冷却效果，而且没有味道。此外，(-)-薄荷醇 β-d-葡萄糖苷在人体细胞系活化试验的皮肤过敏测试中被确定为非致敏物，而薄荷醇则是致敏物。
• 289. The synthesis of conjugated hexuronic acids
  作者：C. A. Marsh

  DOI：10.1039/jr9520001578

  日期：——
• Helferich; Weis, Chemische Berichte, 1956, vol. 89, p. 314,319
  作者：Helferich、Weis

  DOI：——

  日期：——