methyl β-D-galactopyranosyl-(1->6)-β-D-glucopyranoside | 117895-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl β-D-galactopyranosyl-(1->6)-β-D-glucopyranoside
• 英文别名: Methyl 6-O-(β-D-galactopyranosyl)-β-D-glucopyranoside；β-D-Gal-(1->6)-β-D-Glc-OMe；methyl β-allolactoside；Gal(b1-6)b-Glc1Me；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methoxy]oxane-3,4,5-triol
• CAS: 117895-03-1
• 化学式: C₁₃H₂₄O₁₁
• 分子量: 356.327
• InChiKey: ZQPVHVKWCGZNDW-OMVGRNSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl β-D-galactopyranosyl-(1->6)-β-D-glucopyranoside 在 吡啶 作用下， 反应 2.0h， 以79%的产率得到methyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  使用螺旋果肉α-（1→2）-l-半乳糖基转移酶快速有效地合成新型的l-岩藻糖基化三糖同源系列

  摘要：

  来自葡萄园蜗牛螺旋藻的蛋白腺的α-（1-> 2）-L-半乳糖基转移酶表现出高的α-（1-> 2）-L-岩藻糖基转移酶活性，可用于从中转移L-岩藻糖GDP-L-岩藻糖可连接至寡糖的末端非还原D-半乳糖残基，因此可轻松接入各种含H抗原的寡糖。酶促糖基化在这里以毫克级施加到一系列二糖受体底物上。显然，末端和亚末端受体糖单元之间糖苷间键合的位置几乎没有影响。由此产生的三糖的同源系列通过其过乙酸盐的NMR分析得到充分表征。

  DOI：

  10.1016/s0008-6215(03)00344-6
• 作为产物：
  描述：

  甲基 Β-D-吡喃葡萄糖苷 在 palladium on activated charcoal 吡啶 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 sodium hydride 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -10.0~100.0 ℃ 、275.79 kPa 条件下， 反应 100.67h， 生成 methyl β-D-galactopyranosyl-(1->6)-β-D-glucopyranoside
  参考文献：
  名称：

  Sadozai, Khalid Khan; Anand, Jasbir Kaur; Hakomori, Sen-itiroh, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 7, p. 1037 - 1050

  摘要：

  DOI：

文献信息

• Enzymic .beta.-Galactosidation of Modified Monosaccharides: Study of the Enzyme Selectivity for the Acceptor and Its Application to the Synthesis of Disaccharides
  作者：Rosa Lopez、Alfonso Fernandez-Mayoralas

  DOI：10.1021/jo00083a013

  日期：1994.2

  The selectivity of the E. coli beta-galactosidase-catalyzed glycosylation of monosaccharides differently substituted at the anomeric position has been studied. Substituents bearing a phenyl ring increase the enzyme-acceptor binding; however, partial enzyme inhibition occurs. The regioselectivity of the glycosylation was dependent on small variations in the monosaccharide accceptor, such as the atom linked to the anomeric carbon and the number of methylenes between this atom and aromatic ring. A schematic model is proposed that accounts for the results. The information from this study allows the direct synthesis of disaccharides, with high regioselectivity and yields ranging from 30 to 40%.
• The Function of the 5-Hydroxymethyl Group of Lactose in Enzymatic Hydrolysis with beta-Galactosidase from E. coli.
  作者：Kim Adelhorst、Klaus Bock、S. T. Thiilborg、H. M. Nielsen、Fatima M. Piedade、M. M. Kady、S. Brøgger Christensen

  DOI：10.3891/acta.chem.scand.46-1114

  日期：——

  A series of 6-substituted methyl lactoside derivatives together with methyl allolactoside and (6S)-methyl [6-H-2]lactoside have been synthesized and characterized by NMR spectroscopy. All compounds were tested as substrates for the enzyme beta-galactosidase from E. coli using progress curve kinetic methology both in single-substrate and competition experiments. The results show that the hydrolysis of methyl lactoside to a large extent takes place through an intramolecular trans-glycosidation reaction via allolactoside. Furthermore, methyl 6-amino-6-deoxy-D-glucopyranoside proved to be an inhibitor for the enzymatic hydrolysis.
• Enzymatic α(1→2)-l-fucosylation: investigation of the specificity of the α(1→2)-l-galactosyltransferase from Helix pomatia
  作者：Angela Michelle Scheppokat、Minoru Morita、Joachim Thiem、Hagen Bretting

  DOI：10.1016/s0957-4166(03)00521-4

  日期：2003.8

  The alpha(1-->2)-L-galactosyltransferase from Helix pomatia transfers an L-fucosyl residue from GDP-L-Fucose to a terminal, non-reducin D-galactopyranosyl moiety of an oligosaccharide. The extent of the enzyme's specificity towards the stereochemistry at the D-galactopyranosyl anomeric centre, the site of interglycosidic linkage and the nature of the subterminal oliaosaccharide residue has been investigated using HPAEC-PAD and MALDI-TOF technology. This alpha(1-->2)-L-galactosyltransferase is specific for D-galactopyranosyl beta-linkages, independent of the site of the interglycosidic linkage and aglycone configuration and with limited specificity for the nature of the subterminal sugar residue. (C) 2003 Elsevier Ltd. All rights reserved.
• Regioselectivity of β-d-galactosyl-disaccharide formation using the β-d-galactosidase from Bacillus circulans
  作者：Taichi Usui、Shigenori Morimoto、Yukie Hayakawa、Mitsuaki Kawaguchi、Takeomi Murata、Yoshiharu Matahira、Yoshiro Nishida

  DOI：10.1016/s0008-6215(96)90164-0

  日期：1996.5
• Sadozai, Khalid Khan; Anand, Jasbir Kaur; Hakomori, Sen-itiroh, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 7, p. 1037 - 1050
  作者：Sadozai, Khalid Khan、Anand, Jasbir Kaur、Hakomori, Sen-itiroh

  DOI：——

  日期：——