1-β-D-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy-2’,3’,4’,6’-tetracetyl]galactose | 28152-35-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-β-D-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy-2’,3’,4’,6’-tetracetyl]galactose
• 英文别名: 1,2-isopropylidene-3-O-(β-D-2',3',4',6'-tetra-O-acetyl-galactopyranosyl)-rac-glycerol；1,2-O-isopropylidene-3-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)glycerol；1,2-isopropylidene-3-O-(β-2',3',4',6'-tetra-O-acetylgalactopyranosyl)-rac-glycerol；2,3-(isopropylidenedioxy)propyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]oxan-2-yl]methyl acetate
• CAS: 28152-35-4；34382-08-6；34382-09-7；35880-28-5；76249-54-2；130793-62-3
• 化学式: C₂₀H₃₀O₁₂
• 分子量: 462.451
• InChiKey: JLGOOOITHPUWCR-OKQJSRGQSA-N

物化性质

• 沸点：
  508.1±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-β-D-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy-2’,3’,4’,6’-tetracetyl]galactose 在 4-二甲氨基吡啶 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 25.5h， 生成 1,2-O-dilinoleoyl-3-O-(β-D-2',3',4',6'-tetra-O-acetyl-galactopyranosyl)-rac-glycerol
  参考文献：
  名称：

  Synthesis and anti-herpes simplex viral activity of monoglycosyl diglycerides

  摘要：

  Based on the discovery of antiviral beta-galactosyl diglycerides from Clinacanthus nutans leaves, 19 monoglycosyl diglycerides were synthesized and examined for inhibitory effect on herpes simplex virus types I and 2 (HSV-1, HSV-2). A study of the structure-activity relationships of the synthetic monoglycosyl diglycerides indicated that the fatty acyl moieties were critical for inhibitory action with higher activity displayed as the acyl groups became more olefinic in character. The sugar moiety was also important for anti-HSV action; however, the type of sugar (glucose or galactose) did not affect activity. The stereochemistry at C-2 of the glycerol backbone displayed no significant effect on anti-HSV activity. Among the compounds synthesized, 1,2-O-dilinolenoyl-3-O-beta-D-glucopyranosyl-sn-glycerol showed the highest inhibitory activity against HSV-1 and HSV-2 with IC50 values of 12.5 +/- 0.5 and 18.5 +/- 1.5 mug/ml, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2003.09.008
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 silver carbonate 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 24.67h， 生成 1-β-D-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy-2’,3’,4’,6’-tetracetyl]galactose
  参考文献：
  名称：

  Cross-utilization of β-galactosides and cellobiose in Geobacillus stearothermophilus

  摘要：

  Strains of the Gram-positive, thermophilic bacteriumGeobacillus stearothermophiluspossess elaborate systems for the utilization of hemicellulolytic polysaccharides, including xylan, arabinan, and galactan. These systems have been studied extensively in strains T-1 and T-6, representing microbial models for the utilization of soil polysaccharides, and many of their components have been characterized both biochemically and structurally. Here, we characterized routes by whichG. stearothermophilusutilizes mono- and disaccharides such as galactose, cellobiose, lactose, and galactosyl-glycerol. TheG. stearothermophilusgenome encodes a phosphoenolpyruvate carbohydrate phosphotransferase system (PTS) for cellobiose. We found that the cellobiose-PTS system is induced by cellobiose and characterized the corresponding GH1 6-phospho-beta-glucosidase, Cel1A. The bacterium also possesses two transport systems for galactose, a galactose-PTS system and an ABC galactose transporter. The ABC galactose transport system is regulated by a three-component sensing system. We observed that both systems, the sensor and the transporter, utilize galactose-binding proteins that also bind glucose with the same affinity. We hypothesize that this allows the cell to control the flux of galactose into the cell in the presence of glucose. Unexpectedly, we discovered thatG. stearothermophilusT-1 can also utilize lactose and galactosyl-glycerol via the cellobiose-PTS system together with a bifunctional 6-phospho-beta-gal/glucosidase, Gan1D. Growth curves of strain T-1 growing in the presence of cellobiose, with either lactose or galactosyl-glycerol, revealed initially logarithmic growth on cellobiose and then linear growth supported by the additional sugars. We conclude that Gan1D allows the cell to utilize residual galactose-containing disaccharides, taking advantage of the promiscuity of the cellobiose-PTS system.

  DOI：

  10.1074/jbc.ra120.014029

文献信息

• Chemoenzymatic synthesis and antimicrobial activity evaluation of monogalactosyl diglycerides
  作者：Francesca Cateni、Paolo Bonivento、Giuseppe Procida、Marina Zacchigna、Luciana Gabrielli Favretto、Giuditta Scialino、Elena Banfi

  DOI：10.1016/j.ejmech.2007.03.012

  日期：2008.1

  examined for antimicrobial activity against Gram positive, Gram negative bacteria and fungi. The study of their in vitro antimicrobial activity confirms the significant activity of some monogalactosyl diacylglycerol analogues and establishes for the galactose series that the 1,2-disubstitution and the octanoyl chain are the proper structural features for the maximum activity.

  制备具有中等至长脂肪酸酰基链的单半乳糖甘油二酯，并检查其对革兰氏阳性，革兰氏阴性细菌和真菌的抗菌活性。对它们的体外抗菌活性的研究证实了某些单半乳糖基二酰基甘油类似物的显着活性，并为半乳糖系列确定了1,2-二取代基和辛酰基链是最大活性的适当结构特征。
• Chemoenzymatic synthesis and in vitro studies on the hydrolysis of antimicrobial monoglycosyl diglycerides by pancreatic lipase
  作者：Francesca Cateni、Paolo Bonivento、Giuseppe Procida、Marina Zacchigna、Giuditta Scialino、Elena Banfi

  DOI：10.1016/j.bmcl.2007.01.019

  日期：2007.4

  Monoglucosyl and monogalactosyl diglycerides (MGDGs) with medium-long length acyl chains, identified as active components in Euphorbiaccae, were synthesized. They were examined for antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. MGDGs with two octanoyl groups at both 1- and 2-positions showed the most potent activity. The stereoselectivity of pancreatic lipase was investigated in vitro where the preference for the 1 position in MGDGs is strictly related to the length of the acyl chains. (c) 2007 Elsevier Ltd. All rights reserved.
• Werschkun, Barbara; Koenig, Wilfried A.; Kren, Vladimir, Journal of the Chemical Society. Perkin transactions I, 1995, # 19, p. 2459 - 2466
  作者：Werschkun, Barbara、Koenig, Wilfried A.、Kren, Vladimir、Thiem, Joachim

  DOI：——

  日期：——
• Design and synthesis of fluorescent galactolipid probes
  作者：Emiliano Manzo、Giuliana D’Ippolito、Dario Pagano、Francesco Tinto、Angelo Fontana

  DOI：10.1016/j.tetlet.2014.04.059

  日期：2014.6
• An efficient and versatile chemical synthesis of bioactive glyco-glycerolipids
  作者：Emiliano Manzo、Maria Letizia Ciavatta、Dario Pagano、Angelo Fontana

  DOI：10.1016/j.tetlet.2011.12.030

  日期：2012.2

  Synthesis of beta-glyco-1,2-diacylglycerols is achieved by a versatile and simple procedure based on trichloro-acetimidate methodology and use of peracetate sugar substrates. The chemical strategy was tested through stereoselective preparation of beta-galacto- and beta-gluco-lipid derivatives capable to trigger immune system response. The synthetic approach is designed to obtain enantiomerically pure regio- and stereo-isomers including derivatives containing poly-unsaturated fatty acids. (C) 2011 Elsevier Ltd. All rights reserved.