6-O-acetyl-D-glucose | 118759-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-acetyl-D-glucose
• 英文别名: 6-O-acetyl-D-glucopyranose；[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl acetate
• CAS: 118759-70-9
• 化学式: C₈H₁₄O₇
• 分子量: 222.195
• InChiKey: ILLOJQCWUBEHBA-KEWYIRBNSA-N

物化性质

• 熔点：
  135 °C
• 沸点：
  395.8±42.0 °C(Predicted)
• 密度：
  1.553±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  正丁醇 、 6-O-acetyl-D-glucose 在 rutinosidase from Aspergillus niger 作用下， 以 aq. buffer 为溶剂， 生成 槲皮素 、
  参考文献：
  名称：

  扩展芸香苷酶的多功能性：酰化槲皮素吡喃葡萄糖苷作为底物

  摘要：

  黑曲霉芦丁糖苷酶 (AnRut) 有效地裂解芦丁糖模拟物文库 - 在其葡萄糖基部分的 C-6' 处酰化的异槲皮苷。测试的底物包括在葡萄糖基C-6'处被乙酰基、苯甲酰基、苯乙酰基、苯丙酰基、肉桂基、香草基、没食子酰基、4-羟基苯甲酰基和3-(4-羟基-3-O-甲基苯基)丙酰基取代的异槲皮苷。 AnRut 显示出与底物 6'-O-乙酰基异槲皮苷和 6'-O-苯甲酰基异槲皮苷底物进行糖基转移的能力，得到正丁基 6-乙酰基-β-d-吡喃葡萄糖苷和正丁基 6-苯甲酰基-β-d -吡喃葡萄糖苷。

  DOI：

  10.1002/cctc.202400028
• 作为产物：
  描述：

  1,2,3,4-tetra-O-trimethylsilyl-D-glucopyranose 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 6-O-acetyl-D-glucose
  参考文献：
  名称：

  Design and synthesis of the ring-opened derivative of 3-n-butylphthalide-ferulic acid-glucose trihybrids as potential anti-ischemic agents

  摘要：

  To improve aqueous solubility and anti-ischemic activity of 3-n-butylphthalide (NBP), we designed and synthesized the ring-opened derivative of NBP-ferulic acid-glucose trihybrids (S1-S8). These hybrids inhibited adenosine diphosphate (ADP)- or arachidonic acid (AA)-induced platelet aggregation, among them, S2 was 30-fold more water-soluble, and over 10-fold more potent in inhibition of platelet aggregation, as well as reduced ROS generation and protected primary neuronal cells from OGD/R-induced damage, in comparison with NBP. Additionally, S2 was more active than its three moieties alone or in combination, suggesting that the activity of S2 may be attributed to the synergistic effects of these moieties. Importantly, in vivo studies indicated that S2 not only possessed good pharmacokinetic profile, but also improved NBP distribution in rodent brain, suggesting that the glucose moiety in S2 may be recognized by glucose transporter 1 (GLUT1) on blood-brain barrier (BBB), promoting it to penetrate through BBB. Our findings suggest that S2 may be a promising candidate for the intervention of ischemic stroke, warranting further study. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2020.02.031

文献信息

• Carbohydrate esterases of family 2 are 6-<i>O</i>-deacetylases
  作者：Evangelos Topakas、Sarantos Kyriakopoulos、Peter Biely、Ján Hirsch、Christina Vafiadi、Paul Christakopoulos

  DOI：10.1016/j.febslet.2009.11.095

  日期：2010.2.5

  regioselectivity is different from that of typical acetylxylan esterases (AcXEs). In aqueous medium saturated with vinyl acetate, the CE‐2 enzymes catalyzed transacetylation to the same position, i.e., to the primary hydroxyl group of mono‐ and disaccharides. Xylose and xylooligosaccharides did not serve as acetyl group acceptors, therefore the CE‐2 enzymes appear to be 6‐O‐deacetylases.

  测试了来自腐生细菌 Cellvibrio japonicus 和热纤梭菌（碳水化合物酯酶 (CE) 家族 2 的成员）的三种乙酰酯酶 (AcE) 对一系列模型底物的活性，包括部分乙酰化的葡萄糖苷、甘露糖苷和吡喃木糖苷。所有三种酶都表现出对己醛糖 6 位脱乙酰化的强烈偏好。这种区域选择性不同于典型的乙酰木聚糖酯酶 (AcXE)。在醋酸乙烯饱和的水性介质中，CE-2 酶催化乙酰基转移到相同的位置，即到单糖和二糖的伯羟基。木糖和低聚木糖不作为乙酰基受体，因此 CE-2 酶似乎是 6-O-脱乙酰酶。
• Highly Efficient Synthesis of Glucose Fatty Acid Esters Catalyzed by High Performance Lipase Preparations
  作者：Benu Arora

  DOI：10.14233/ajchem.2021.23391

  日期：——

  Glucose fatty acid esters were synthesized using cross-linked enzyme aggregates (CLEAs), protein coated microcrystals (PCMCs) and cross-linked protein coated microcrystals (CLPCMCs) of Candida antarctica lipase B (CALB) as biocatalyst designs in single and mixed solvent systems. Up to 90% conversion and more than 99% regioselectivity were obtained using vinyl acetate as the acyl donor in a solvent system composed of 2-methyl-2-butanol (2M2B) and 30% (v/v) DMSO, with CALB CLEAs within 45 min. Similar results were obtained with CALB CLPCMCs as the biocatalyst under the same reaction conditions. This approach was then extended to the synthesis of glucose esters with higher acyl chain length. The synthetic strategy used in this work can potentially be extended for the fast and regioselective esterification/transesterification of other sugars as well.

  使用交联酶聚集体（CLEAs）、蛋白质包被微晶（PCMCs）和交联蛋白质包被微晶（CLPCMCs）作为生物催化剂设计，在单一和混合溶剂系统中合成了葡萄糖脂肪酸酯。使用乙酸乙烯酯作为酰基供体，在由2-甲基-2-丁醇（2M2B）和30%（v/v）DMSO组成的溶剂系统中，使用CALB CLEAs在45分钟内获得了高达90%的转化率和超过99%的区域选择性。在相同的反应条件下，使用CALB CLPCMCs作为生物催化剂也获得了类似的结果。然后将这种方法扩展到合成具有更高酰链长度的葡萄糖酯。本研究中使用的合成策略还可以潜在地扩展到其他糖的快速和区域选择性酯化/转酯化。
• Bhattacharya, A; Ali, E, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 12, p. 898 - 899
  作者：Bhattacharya, A、Ali, E

  DOI：——

  日期：——
• Organoboron-Disaccharides; II¹. 2,6-Anhydro-β-D-fructofuranose by<i>O</i>-Ethylboron-Induced Cleavage of Sucrose
  作者：Kalulu M. Taba、Roland Köster、Wilhelm V. Dahlhoff

  DOI：10.1055/s-1983-30618

  日期：——
• Differential activities of a lipase and a protease toward straight- and branched-chain acyl donors in transesterification to carbohydrates in an organic medium
  作者：Takashi Watanabe、Rika Matsue、Yoichi Honda、Masaaki Kuwahara

  DOI：10.1016/0008-6215(95)00151-i

  日期：1995.9