α-L-fucopyranosyl-(1->2)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-D-glucopyranose | 34852-43-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-L-fucopyranosyl-(1->2)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-D-glucopyranose
• 英文别名: O-α-L-fucopyranosyl-(1->2)-O-β-D-galactopyranosyl-(1->4)-O-<α-L-fucopyranosyl-(1->3)>-β-D-glucose；4-O-[2-O-(α-L-fucopyranosyl)-β-D-galactopyranosyl]-3-O-(α-L-fucopyranosyl)-β-D-glucopyranose；difucosyllactose；3,2'-difucosyllactose；α-L-Fuc-(1→2)-β-D-Gal-(1→4)-[α-L-Fuc-(1→3)]-β-D-Glc；Difucosyllactose；(2S,3S,4R,5S,6S)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-5,6-dihydroxy-2-(hydroxymethyl)-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 34852-43-2
• 化学式: C₂₄H₄₂O₁₉
• 分子量: 634.586
• InChiKey: LKOHREGGXUJGKC-GXSKDVPZSA-N

物化性质

• 沸点：
  930.8±65.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  307
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  α-L-fucopyranosyl-(1->2)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-D-glucopyranose 在 氨基甲酸铵 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 103.0h， 生成 N-(N-benzyloxycarbonylglycyl)-4-O-[2-O-(α-L-fucopyranosyl)-β-D-galactopyranosyl]-3-O-(α-L-fucopyranosyl)-D-glucopyranosyl amine
  参考文献：
  名称：

  Synthesis of N-glycyl-β-glycopyranosyl amines, derivatives of natural oligosaccharides — glucose analogs of Lex antigen

  摘要：

  对天然三糖、四糖和五糖（β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-d-Glcp、α-l-Fucp-(1→2)-β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-d-Glcp和α-l-Fucp-(1→2)-[α-d-GalNAcp-(1→3)]-β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-d-Glcp）进行处理，它们是Lex的葡萄糖类似物，与甲醇中的氨基甲酸铵反应，得到相应的β-吡喃糖胺。用N-Z-甘氨酸N-羟基琥珀酰亚胺酯（Z为苄氧羰基）进行N-酰化，随后通过氢解去除Z基团，得到相应的N-甘氨酰-β-吡喃糖胺，收率高达70%。

  DOI：

  10.1007/s11172-014-0461-6
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 反应 0.5h， 生成 α-L-fucopyranosyl-(1->2)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-D-glucopyranose 、 O-α-L-fucopyranosyl-(1->2)-O-β-D-galactopyranosyl-(1->4)-O-<α-L-fucopyranosyl-(1->3)>-α-D-glucose
  参考文献：
  名称：

  Synthesis of 3- and 2′-fucosyl-lactose and 3,2′-difucosyl-lactose from partially benzylated lactose derivatives

  摘要：

  DOI：

  10.1016/s0008-6215(00)90025-9

文献信息

• Bioorthogonal human milk oligosaccharide probes for antimicrobial target identification within Streptococcus agalactiae
  作者：Schuyler A. Chambers、Steven D. Townsend

  DOI：10.1016/j.carres.2019.107895

  日期：2020.2

  Human milk oligosaccharides (HMOs) are a structurally diverse class of carbohydrates that possess strong antibacterial activity against Streptococcus agalactiae (Group B Strep, GBS). This work highlights the design, synthesis, and retained biological activity of several HMO bioorthogonal probes within GBS, a first in class advance. The use of such probes will assist in identifying HMO-protein interactions within GBS and may be broadly applicable in researching HMO cellular targets within a variety of biological systems. Finally, this strategy is highly amenable to other oligosaccharide scaffolds, requiring minimal synthetic transformations and chemical perturbation.
• Synthesis of 3- and 2′-fucosyl-lactose and 3,2′-difucosyl-lactose from partially benzylated lactose derivatives
  作者：Alfonso Fernandez-Mayoralas、Manuel Martin-Lomas

  DOI：10.1016/s0008-6215(00)90025-9

  日期：1986.10
• Synthesis of N-glycyl-β-glycopyranosyl amines, derivatives of natural oligosaccharides — glucose analogs of Lex antigen
  作者：L. M. Likhosherstov、O. S. Novikova、N. G. Kolotyrkina、I. A. Yamskov、V. E. Piskarev

  DOI：10.1007/s11172-014-0461-6

  日期：2014.2

  Treatment of the natural tri-, tetra-, and pentasaccharides, β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-d-Glcp, α-l-Fucp-(1→2)-β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-d-Glcp, and α-l-Fucp-(1→2)-[α-d-GalNAcp-(1→3)]-β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-d-Glcp, which are glucose analogs of Lex, with ammonium carbamate in aqueous methanol gave the corresponding β-glycopyranosyl amines. After their N-acylation with N-Z-glycine N-hydroxysuccinimidyl ester (Z is benzyloxycarbonyl) with subsequent hydrogenolytic removal of Z-group, corresponding N-glycyl-β-glycopyranosyl amines were obtained in yields up to 70%.

  对天然三糖、四糖和五糖（β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-d-Glcp、α-l-Fucp-(1→2)-β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-d-Glcp和α-l-Fucp-(1→2)-[α-d-GalNAcp-(1→3)]-β-d-Galp-(1→4)-[α-l-Fucp-(1→3)]-d-Glcp）进行处理，它们是Lex的葡萄糖类似物，与甲醇中的氨基甲酸铵反应，得到相应的β-吡喃糖胺。用N-Z-甘氨酸N-羟基琥珀酰亚胺酯（Z为苄氧羰基）进行N-酰化，随后通过氢解去除Z基团，得到相应的N-甘氨酰-β-吡喃糖胺，收率高达70%。