3-O-[6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,4-tri-O-benzyl-β-D-galactopyranosyl]-1,2-O-sn-glycerol | 57731-86-9

• 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: 3-O-[6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,4-tri-O-benzyl-β-D-galactopyranosyl]-1,2-O-sn-glycerol
• 英文别名: 3-O-[6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,4-tri-O-benzyl-β-D-galactopyranosyl]-sn-glycerol；(2R)-3-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-[[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropane-1,2-diol
• CAS: 57731-86-9
• 化学式: C₆₄H₇₀O₁₃
• 分子量: 1047.25
• InChiKey: UUOPRPSFNBENRC-CEIHLXNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  77
• 可旋转键数：
  29
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3-O-[6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,4-tri-O-benzyl-β-D-galactopyranosyl]-1,2-O-sn-glycerol 、 月桂酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到3-O-[6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,4-tri-O-benzyl-β-D-galactopyranosyl]-1,2-di-O-dodecanoyl-sn-glycerol
  参考文献：
  名称：

  Syntheses of an α-d-Gal-(1→6)-β-d-Gal diglyceride, as lipase substrate

  摘要：

  Two different routes were explored to afford 3-O-(6-0-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-1,2-di-O-dodecanoyl-sn-glycerol. In the first one, the key step was the glycosylation of the 3-O-(2,3,4-tri-O-benzyl-beta-D-galactopyranosyl)- 1, 2-O-isopropylidene-sn-glycerol acceptor with 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside as the donor. In the second one, the key step was the coupling of 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-D-galactopyranosyl trichloroacetimidate donor with 1,2-O-isopropylidene-sn-glycerol. Even though the number of steps was the same in both pathways, the first one afforded a better overall yield (12.4%) than the second one (6.5%). This eight-step synthesis allowed the preparation of the expected glycolipid, which was used as substrate for recombinant GPLRP2 galactolipase using the monomolecular film technique. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.021
• 作为产物：
  描述：

  2',3',4',6'-tetra-O-acetyl-1'-O-β-D-galactopyranosyl-(2S,3)-isopropylidene-glycerol 在 咪唑 、 4 A molecular sieve 、 四丁基氟化铵 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 115.0h， 生成 3-O-[6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,4-tri-O-benzyl-β-D-galactopyranosyl]-1,2-O-sn-glycerol
  参考文献：
  名称：

  Syntheses of an α-d-Gal-(1→6)-β-d-Gal diglyceride, as lipase substrate

  摘要：

  Two different routes were explored to afford 3-O-(6-0-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-1,2-di-O-dodecanoyl-sn-glycerol. In the first one, the key step was the glycosylation of the 3-O-(2,3,4-tri-O-benzyl-beta-D-galactopyranosyl)- 1, 2-O-isopropylidene-sn-glycerol acceptor with 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside as the donor. In the second one, the key step was the coupling of 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-D-galactopyranosyl trichloroacetimidate donor with 1,2-O-isopropylidene-sn-glycerol. Even though the number of steps was the same in both pathways, the first one afforded a better overall yield (12.4%) than the second one (6.5%). This eight-step synthesis allowed the preparation of the expected glycolipid, which was used as substrate for recombinant GPLRP2 galactolipase using the monomolecular film technique. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.021

文献信息

• Lipolysis of natural long chain and synthetic medium chain galactolipids by pancreatic lipase-related protein 2
  作者：Sawsan Amara、Nathalie Barouh、Jérôme Lecomte、Dominique Lafont、Sylvie Robert、Pierre Villeneuve、Alain De Caro、Frédéric Carrière

  DOI：10.1016/j.bbalip.2010.01.003

  日期：2010.4

  densitometry and gas chromatography. The optimum assay conditions for hydrolysis of these natural long chain galactolipids were investigated and the optimum bile salt to substrate ratio was found to be different from that established with synthetic medium chains MGDG and DGDG. Nevertheless the length of acyl chains and the nature of the galactosyl polar head of the galactolipid did not have major effects

  单半乳糖基二酰基甘油（MGDG）和二半乳糖基二酰基甘油（DGDG）是自然界中最丰富的脂质，主要作为植物叶片和叶绿体膜的重要成分。先前发现胰腺脂肪酶相关蛋白2（PLRP2）具有半乳糖脂酶活性，并且被认为是消化道中这些常见植物脂质消化的主要酶。但是，以前的大多数体外研究都是以中链合成半乳糖脂为底物进行的。此处显示重组豚鼠（Cavia porcellus）以及从菠菜叶中提取的高水解率的天然DGDG和MGDG水解的人PLRP2。通过将pH值统计技术，薄层色谱法与扫描光密度法和气相色谱法相结合，可以估算其比活性。研究了水解这些天然长链半乳糖脂的最佳测定条件，发现最佳胆汁盐与底物的比率不同于合成中链MGDG和DGDG所确定的比率。然而，酰基链的长度和半乳糖脂的半乳糖基极性头的性质对PLRP2的比活性没有重大影响，在两个中链上均发现PLRP2的比活性非常高[1786±100至5420±85 U /毫克]
• Syntheses of an α-d-Gal-(1→6)-β-d-Gal diglyceride, as lipase substrate
  作者：Dominique Lafont、Frédéric Carrière、Francine Ferrato、Paul Boullanger

  DOI：10.1016/j.carres.2006.01.021

  日期：2006.5

  Two different routes were explored to afford 3-O-(6-0-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-1,2-di-O-dodecanoyl-sn-glycerol. In the first one, the key step was the glycosylation of the 3-O-(2,3,4-tri-O-benzyl-beta-D-galactopyranosyl)- 1, 2-O-isopropylidene-sn-glycerol acceptor with 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside as the donor. In the second one, the key step was the coupling of 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-D-galactopyranosyl trichloroacetimidate donor with 1,2-O-isopropylidene-sn-glycerol. Even though the number of steps was the same in both pathways, the first one afforded a better overall yield (12.4%) than the second one (6.5%). This eight-step synthesis allowed the preparation of the expected glycolipid, which was used as substrate for recombinant GPLRP2 galactolipase using the monomolecular film technique. (c) 2006 Elsevier Ltd. All rights reserved.