Methyl 2-O-(β-D-galactopyranosyl)-β-D-glucopyranoside | 144722-08-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2-O-(β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: Gal(b1-2)b-Glc1Me；(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 144722-08-7
• 化学式: C₁₃H₂₄O₁₁
• 分子量: 356.327
• InChiKey: YUAFWDJFJCEDHL-PFOMBOSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 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：

  Methyl 2-O-(β-D-galactopyranosyl)-β-D-glucopyranoside 、 5`-二磷酸鸟嘌呤核苷-岩藻糖二钠盐 在 Helix pomatia albumen gland sediment sodium azide 、 calf intestine alkaline phosphatase EC 3.1.3.1 、 manganese(ll) chloride 作用下， 以 various solvent(s) 为溶剂， 反应 18.0h， 以75%的产率得到Fuc(a1-2)Gal(b1-2)b-Glc1Me
  参考文献：
  名称：

  Enzymatic α(1→2)-l-fucosylation: investigation of the specificity of the α(1→2)-l-galactosyltransferase from Helix pomatia

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(03)00521-4
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0~41.0 ℃ 、101.33 kPa 条件下， 反应 40.0h， 生成 Methyl 2-O-(β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  甲基α-和β-d-吡喃葡萄糖苷的2,3-二-O-糖基衍生物的合成

  摘要：

  摘要描述了具有α-d-甘露聚糖-，β-d-半乳糖-，α-1-rhamno-，α-的甲基α-和β-d-吡喃葡萄糖苷的2,3-二-O-糖基衍生物的合成。在O-2和O-3处的1-fuco-和β-1-fuco-吡喃糖基取代基。合成涉及甲基4,6-O-（亚苄基-α-（24）和β-d-吡喃葡萄糖苷（21）以及21位带有2-O-（2,3,4,6-tetra的衍生物）的糖基化-O-苄基-α-d-甘露吡喃糖基）-，-（2,3,4,6-四-O-乙酰基-β-d-吡喃半乳糖基）-，-（2,3,4-三-O-苯甲酚-α-L-鼠李糖基）-和-（2,3,4-三-O-苯甲酰基-β-1-呋喃果糖基）基团。

  DOI：

  10.1016/0008-6215(93)84002-n

文献信息

• Fast and efficient synthesis of a novel homologous series of l-fucosylated trisaccharides using the Helix pomatia α-(1→2)-l-galactosyltransferase
  作者：Angela Michelle Scheppokat、Hagen Bretting、Joachim Thiem

  DOI：10.1016/s0008-6215(03)00344-6

  日期：2003.9

  The alpha-(1-->2)-L-galactosyltransferase from the albumen gland of the vineyard snail Helix pomatia exhibits high alpha-(1-->2)-L-fucosyltransferase activity and can be used to transfer L-fucose from GDP-L-fucose to terminal, non-reducing D-galactose residues of an oligosaccharide, thus providing facile access to a range of H-antigen-containing oligosaccharides. The enzymatic glycosylation was applied

  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。
• 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：——
• Synthesis of 2,3-di-O-glycosyl derivatives of methyl α- and β-d-glucopyranoside
  作者：Nikolay E. Nifant'ev、Vera Yu. Amochaeva、Alexander S. Shashkov、Nikolay K. Kochetkov

  DOI：10.1016/0008-6215(93)84002-n

  日期：1993.12

  Abstract The syntheses are described of 2,3-di- O -glycosyl derivatives of methyl α- and β- d -glucopyranoside having α- d -manno-, β- d -galacto-, α- l -rhamno-, α- l -fuco-, and β- l -fuco-pyranosyl substitutents at O-2 and O-3. The syntheses involved glycoslation of methyl 4,6- O -(benzylidene-α- ( 24 ) and β- d -glucopyranoside ( 21 ), and substituted derivatives of 21 bearing 2- O -(2,3,4,6-tetra-

  摘要描述了具有α-d-甘露聚糖-，β-d-半乳糖-，α-1-rhamno-，α-的甲基α-和β-d-吡喃葡萄糖苷的2,3-二-O-糖基衍生物的合成。在O-2和O-3处的1-fuco-和β-1-fuco-吡喃糖基取代基。合成涉及甲基4,6-O-（亚苄基-α-（24）和β-d-吡喃葡萄糖苷（21）以及21位带有2-O-（2,3,4,6-tetra的衍生物）的糖基化-O-苄基-α-d-甘露吡喃糖基）-，-（2,3,4,6-四-O-乙酰基-β-d-吡喃半乳糖基）-，-（2,3,4-三-O-苯甲酚-α-L-鼠李糖基）-和-（2,3,4-三-O-苯甲酰基-β-1-呋喃果糖基）基团。
• 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.