Methyl 3-O-(β-D-galactopyranosyl)-β-D-glucopyranoside | 128443-50-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 3-O-(β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: methyl 3-β-D-galactosyl-β-D-glucopyranoside；β-D-Galp-(1->3)-β-D-Glcp-OMe；β-D-Gal-(1'->3)-β-D-Glc-OMe；β-D-Gal-(1->3)-β-D-Glc-OMe；β-Gal-(1→3)-β-Glc-OMe；βGal-(1→3)-βGlc-OMe；Gal(b1-3)b-Glc1Me；(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 128443-50-5
• 化学式: C₁₃H₂₄O₁₁
• 分子量: 356.327
• InChiKey: WOKXHOIRHHAHDA-CKCNBROPSA-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 3-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81%的产率得到(2S,3S,4R,5S,6S)-2-[(2S,3R,4S,5R,6R)-2-((2R,3R,4S,5R,6R)-3,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3,4,5-triol
  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：

  2,3,4,6-四-O-乙酰基-Alpha-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 21.17h， 生成 Methyl 3-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。
• Enzymatic synthesis of α-l-fucosyl-N-acetyllactosamines and 3′-O-α-l-fucosyllactose utilizing α-l-fucosidases
  作者：Takeomi Murata、Shigenori Morimoto、Xiaoxiong Zeng、Satoshi Watanabe、Taichi Usui

  DOI：10.1016/s0008-6215(99)00156-1

  日期：1999.8

  Abstract An α- l -fucosidase from porcine liver produced α- l -Fuc-(1→2)-β- d -Gal-(1→4)- d -GlcNAc (2′-O-α- l -fucosyl-N-acetyllactosamine, 1) together with its isomers α- l -Fuc-(1→3)-β- d -Gal-(1→4)- d -GlcNAc (2) and α- l -Fuc-(1→6)-β- d -Gal-(1→4)- d -GlcNAc (3) through a transglycosylation reaction from p-nitrophenyl α- l -fucopyranoside and β- d -Gal-(1→4)- d -GlcNAc. The enzyme formed the trisaccharides

  摘要猪肝脏的α-岩藻糖苷酶产生α-1-Fuc-（1→2）-β-d-Gal-（1→4）-d-GlcNAc（2′-O-α-l-岩藻糖基- N-乙酰基乳糖胺1）及其异构体α-1-Fuc-（1→3）-β-d-Gal-（1→4）-d-GlcNAc（2）和α-1-Fuc-（1→ 6）-β-d-Gal-（1→4）-d-GlcNAc（3）通过对硝基苯基α-1-呋喃果糖苷和β-d-Gal-（1→4）-d-GlcNAc的转糖基反应。该酶以供体的比例为40:37:23，以总产率的13％形成了三糖1-3。相比之下，Alcaligenes sp。的转糖基化。α-1-岩藻糖苷酶导致包含（1→3）连接的α-1-岩藻糖基残基的三糖的区域选择性合成。当β-d -Gal-（1→4）-d -GlcNAc和乳糖为受体时，酶选择性地形成化合物2和α-1-Fuc-（1→3）-β-d-Gal-（1→4） ）-d -Glc（3'-O-α-l-岩藻糖半乳糖，4），
• Use of molecularly imprinted polymers for stereo- and/or regioselective synthesis
  申请人：Mosbach Klaus

  公开号：US20050027102A1

  公开（公告）日：2005-02-03

  Molecularly imprinted polymers can be utilized in stereo- and regio-selective synthesis. These systems can be utilized, e.g. for peptide synthesis, by selectively coordinating reactants at a predetermined preformed cavity. Further, such polymers may be used for the selective removal of one enantiomeric species from solution, allowing reaction to be directed to another species in bulk solution leading to stereoselective and/or regio-selective synthesis in the cavity of for instance peptides. Additionally, when utilized as regioselectively interacting protectioning matrices, these polymers can direct reaction to an alternate centre of a reacting substrate.

  分子印迹聚合物可用于立体和区域选择性合成。这些系统可以选择性地使反应物在预定的预制空腔中配位，例如用于肽合成。此外，此类聚合物还可用于选择性地去除溶液中的一种对映体，从而将反应引向大体积溶液中的另一种对映体，从而在空腔中进行立体选择性和/或区域选择性合成，例如肽。此外，当用作具有区域选择性相互作用的保护基质时，这些聚合物可将反应引向反应底物的另一个中心。
• 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%.
• 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：——