(2R)-1-O-α-D-glucosylglycerol | 19432-18-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2R)-1-O-α-D-glucosylglycerol
• 英文别名: (2S,3R,4S,5S,6R)-2-((R)-2,3-dihydroxypropoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol；(2S,3R,4S,5S,6R)-2-[(2R)-2,3-dihydroxypropoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 19432-18-9
• 化学式: C₉H₁₈O₈
• 分子量: 254.237
• InChiKey: NHJUPBDCSOGIKX-NZJLWHDDSA-N

物化性质

• 沸点：
  619.2±55.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-O-Alpha-D-吡喃葡萄糖基-D-呋喃果糖 在 lead(IV) acetate 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 8.0h， 生成 (2R)-1-O-α-D-glucosylglycerol
  参考文献：
  名称：

  Identification of α-D-Glucosylglycerol in Sake

  摘要：

  在日本米酒（清酒）中首次发现了约0.5%的α-D-葡萄糖基甘油（GG）。GG还在使用曲霉发酵的味噌和米酒中被发现。GG在与麦芽酶（EC 3.2.1.20，来自酵母的α-葡萄糖苷酶）反应时被水解为等摩尔比的葡萄糖和甘油，但与乳糖酶（EC 3.2.1.21，来自杏仁的β-葡萄糖苷酶）没有反应。通过气相色谱-质谱（GC-MS）分析清酒中GG的三甲基氟基衍生物的保留时间和质谱与通过糖解合成的各种GG样品相当。研究证明清酒中的GG由三个成分组成，即2-O-α-D-葡萄糖基甘油（GG-II）、(2R)-1-O-α-D-葡萄糖基甘油（R-GG-I）和(2S)-1-O-α-D-葡萄糖基甘油（S-GG-I）。在清酒中这三个成分的比例为6:66:28。据信，GG是通过来自曲霉的α-葡萄糖苷酶将葡萄糖基转移到甘油上形成的，发生在清酒发酵浆中。

  DOI：

  10.1271/bbb.64.378

文献信息

• Synthesis of α-<scp>D</scp>-Glucosylglycerol by α-Glucosidase and Some of Its Characteristics
  作者：Fumihito TAKENAKA、Hirofumi UCHIYAMA

  DOI：10.1271/bbb.64.1821

  日期：2000.1

  It has been found that α-D-glucosylglycerol (GG) is contained in such traditional Japanese foods brewed by using koji as sake, miso and mirin, and that GG is formed by transglucosylation to glycerol that is produced by yeast with α-glucosidase (EC 3.2.1.20) from koji in the sake mash. GG has also been found to consist of three components, 2-O-α-D-glucosylglycerol (GG-II), (2R)-1-O-α-D-glucosylglycerol (R-GG-I) and (2S)-1-O-α-D-glucosylglycerol (S-GG-I). GG was synthesized from a mixture of maltose and glycerol by the batch method, using α-glucosidase (transglucosidase L-AMANO). α-Glucosidase seemed to be so stable that the amount of GG increased about 5-fold compared with that in the first reaction by the daily addition of maltose for 10 d. Syrupy GG obtained was found to have the following characteristics: about 0.55-fold sweetness compared with sucrose, high thermo-stability, low heat-colorability, low Maillard reactivity, low hygroscopicity, high water-holding capacity, non-cariogenicity and low digestibility.

  研究发现，清酒、味噌和米林等使用麴酿造的传统日本食品中含有α-D-葡萄糖基甘油（GG），而 GG 是由清酒酒泥中含有α-葡萄糖苷酶（EC 3.2.1.20）的麴酵母经转葡萄糖基作用生成的甘油。研究还发现，甘油三酯由三种成分组成：2-O-α-D-葡萄糖基甘油（GG-II）、(2R)-1-O-α-D-葡萄糖基甘油（R-GG-I）和(2S)-1-O-α-D-葡萄糖基甘油（S-GG-I）。α-葡萄糖苷酶似乎非常稳定，每天添加麦芽糖 10 天，GG 的量比第一次反应增加了约 5 倍。获得的糖浆状 GG 具有以下特点：甜度约为蔗糖的 0.55 倍，热稳定性高，热着色性低，马氏反应性低，吸湿性低，持水量高，无致畸性，消化率低。
• The Inhibition of the Reverse Transcriptase of HIV-1 by the Natural Sulfoglycolipids from Cyanobacteria: Contribution of Different Moieties to Their High Potency
  作者：Shoshanna Loya、Vered Reshef、Erez Mizrachi、Colin Silberstein、Yocheved Rachamim、Shmuel Carmeli、Amnon Hizi

  DOI：10.1021/np970585j

  日期：1998.7.1

  The potent in vitro inhibition of the enzymatic activity of the human immunodeficiency virus-1 (HIV-1) reverse transcriptase (RT) by the lipophilic extracts of cyanobacteria(8) was primarily attributed to the sulfoquinovosylpranosyl lipids, compounds 1-4. These sulfolipids inhibit efficiently and selectively only the DNA polymerase activity of HIV-1 RT (and not the ribonuclease H function) with 50% inhibitory concentration value (IC50) as low as 24 nM exhibited by compound 1. The novel natural compound 4, in which two hydroxy groups on the sugar moiety are substituted by palmitoyl residues, exhibits a significant decrease in the maximal inhibition capacity. It is possible, therefore, that the contribution of acylated groups to the molecule at these positions interferes with inhibition, possibly, by steric hindrance. Both the sulfonic acid moiety and the fatty acid ester side chain have a substantial effect in potentiating the extent of inhibition. For one, the inhibitory effects of all the natural glycolipids tested (5-8) are markedly reduced, and the hydrolysis of the fatty acid side chain, as in derivative 9, has substantially abolished the inhibition of HIV RT.
• Identification of α-<scp>D</scp>-Glucosylglycerol in Sake
  作者：Fumihito TAKENAKA、Hirofumi UCHIYAMA、Takeshi IMAMURA

  DOI：10.1271/bbb.64.378

  日期：2000.1

  α-D-Glucosylglycerol (GG) was found for the first time in sake (Japanese rice wine) in an amount of about 0.5%. GG was also found in miso and mirin which had been brewed by using koji. GG was hydrolyzed into glucose and glycerol in an equimolar ratio with maltase (EC 3.2.1.20, α-glucosidase from yeast), but not with emulsin (EC 3.2.1.21, β-glucosidase from almond). The retention times and mass spectra of trimethylsilyl derivatives by a GC-MS analysis of GG in sake were comparable to those of various GG samples synthesized by glycol cleavage. It was proven that GG in sake consisted of three components, viz., 2-O-α-D-glucosylglycerol (GG-II), (2R)-1-O-α-D-glucosylglycerol (R-GG-I) and (2S)-1-O-α-D-glucosylglycerol (S-GG-I). The ratio of the three components in GG was 6:66:28 for sake. It is considered that GG was formed by transglucosylation of the glucosyl groups to glycerol by α-glucosidase from koji in the sake mash.

  在日本米酒（清酒）中首次发现了约0.5%的α-D-葡萄糖基甘油（GG）。GG还在使用曲霉发酵的味噌和米酒中被发现。GG在与麦芽酶（EC 3.2.1.20，来自酵母的α-葡萄糖苷酶）反应时被水解为等摩尔比的葡萄糖和甘油，但与乳糖酶（EC 3.2.1.21，来自杏仁的β-葡萄糖苷酶）没有反应。通过气相色谱-质谱（GC-MS）分析清酒中GG的三甲基氟基衍生物的保留时间和质谱与通过糖解合成的各种GG样品相当。研究证明清酒中的GG由三个成分组成，即2-O-α-D-葡萄糖基甘油（GG-II）、(2R)-1-O-α-D-葡萄糖基甘油（R-GG-I）和(2S)-1-O-α-D-葡萄糖基甘油（S-GG-I）。在清酒中这三个成分的比例为6:66:28。据信，GG是通过来自曲霉的α-葡萄糖苷酶将葡萄糖基转移到甘油上形成的，发生在清酒发酵浆中。