(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 | 182276-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• 英文别名: Fuc(a1-2)Gal(b1-3)b-Glc1Me；(2S,3S,4R,5S,6S)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 182276-49-9
• 化学式: C₁₉H₃₄O₁₅
• 分子量: 502.47
• InChiKey: PTHOXONVRPSCKT-NPBLXBRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  237
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (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 在 吡啶 作用下， 以2.1 mg的产率得到methyl 2,4,6-tri-O-acetyl-3-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-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：

  beta-D-半乳糖五乙酸酯 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 氰化汞 、 对甲苯磺酸 、 三乙胺 、 mercury dibromide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 36.75h， 生成 (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：

  Synthesis and structural studies of branched 2-linked trisaccharides related to blood group determinants

  摘要：

  A series of trisaccharide glycosides, Fuc-(1 --> 2)-beta-Gal-(1 --> 3)-beta-X-OMe (X = GlcNAc, Glc, 2-deoxy-Glc) related to the blood group determinant Led have been synthesised both as their alpha- and beta-Fuc anomers together with the component disaccharide starting compounds. The conformational properties of the six trisaccharides together with their parent disaccharides have been investigated by NMR spectroscopy (proton and carbon chemical shifts and proton NOEs) in combination with computer modeling using the Monte Carlo approach and the HSEA force field using the GEGOP programme. The interaction between the terminal fucose unit and the reducing unit was probed by substitution of the bulky NAc group with hydroxyl and deoxy substituents, respectively. Compounds with severe steric interactions were identified by the non-additivity of their carbon chemical shifts. This was subsequently confirmed by the detailed conformational assessment by NOE spectroscopy and computer modeling. The most severe contacts arose in the alpha-L-Fuc derivatives, whereas the beta-linked L-Fuc derivatives only in one case exhibit severe steric interaction as probed by the NMR parameters. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0008-6215(96)00103-6

文献信息

• 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.
• Synthesis and structural studies of branched 2-linked trisaccharides related to blood group determinants
  作者：J Duus

  DOI：10.1016/0008-6215(96)00103-6

  日期：1996.7.19

  A series of trisaccharide glycosides, Fuc-(1 --> 2)-beta-Gal-(1 --> 3)-beta-X-OMe (X = GlcNAc, Glc, 2-deoxy-Glc) related to the blood group determinant Led have been synthesised both as their alpha- and beta-Fuc anomers together with the component disaccharide starting compounds. The conformational properties of the six trisaccharides together with their parent disaccharides have been investigated by NMR spectroscopy (proton and carbon chemical shifts and proton NOEs) in combination with computer modeling using the Monte Carlo approach and the HSEA force field using the GEGOP programme. The interaction between the terminal fucose unit and the reducing unit was probed by substitution of the bulky NAc group with hydroxyl and deoxy substituents, respectively. Compounds with severe steric interactions were identified by the non-additivity of their carbon chemical shifts. This was subsequently confirmed by the detailed conformational assessment by NOE spectroscopy and computer modeling. The most severe contacts arose in the alpha-L-Fuc derivatives, whereas the beta-linked L-Fuc derivatives only in one case exhibit severe steric interaction as probed by the NMR parameters. (C) 1996 Elsevier Science Ltd.
• 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。