α-L-fucopyranosyl-(1→3)-α-D-mannopyranose | 1437790-28-7

• 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→3)-α-D-mannopyranose
• 英文别名: Fuc(a1-3)a-Man；(2S,3S,4R,5S,6S)-2-methyl-6-[(2S,3S,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl]oxyoxane-3,4,5-triol
• CAS: 1437790-28-7
• 化学式: C₁₂H₂₂O₁₀
• 分子量: 326.301
• InChiKey: HLLZGYFHHYGOLN-RRZNJPKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  甘露糖 、 4-硝基苯-Α-L-吡喃海藻糖苷 在 α-fucosidase 作用下， 以 aq. acetate buffer 为溶剂， 反应 27.0h， 生成 α-L-fucopyranosyl-(1→3)-α-D-mannopyranose 、 α-L-fucopyranosyl-(1→3)-β-D-mannopyranose
  参考文献：
  名称：

  Preparation of branched cyclomaltoheptaose with 3-O-α-l-fucopyranosyl-α-d-mannopyranose and changes in fucosylation of HCT116 cells treated with the fucose-modified cyclomaltoheptaose

  摘要：

  From a mixture of 4-nitrophenyl alpha-L-fucopyranoside and D-mannopyranose, 3-O-alpha-L-fucopyranosyl-D-mannopyranose was synthesised through the transferring action of alpha-fucosidase (Sumizyme PHY). 6(I), 6(IV)-Di-O-(3-O-alpha-L-fucopyranosyl-alpha-D-mannopyranosyl)-cyclomaltoheptaose {8, 6(I), 6(IV)-di-O-[alpha-L-Fuc(1 -> 3)-alpha-D-Man]-beta CD} was chemically synthesised using the trichloroacetimidate method. The structures were confirmed by MS and NMR spectroscopy. A cell-based assay using the fucosyl beta CD derivatives, including the newly synthesised 8, showed that derivatives with two branches of the alpha-L-Fuc or alpha-L-Fuc(1 -> 3)-alpha-D-Man residues possessed slight growth-promoting effects and lower toxicity in HCT116 cells compared to those with one branch. These compounds may be useful as drug carriers in targeted drug delivery systems. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.022

文献信息

• Preparation of branched cyclomaltoheptaose with 3-O-α-l-fucopyranosyl-α-d-mannopyranose and changes in fucosylation of HCT116 cells treated with the fucose-modified cyclomaltoheptaose
  作者：Madoka Kimura、Yuki Masui、Yuko Shirai、Chie Honda、Kenta Moriwaki、Taku Imai、Uichiro Takagi、Takaaki Kiryu、Taro Kiso、Hiromi Murakami、Hirofumi Nakano、Sumio Kitahata、Eiji Miyoshi、Toshiko Tanimoto

  DOI：10.1016/j.carres.2013.03.022

  日期：2013.6

  From a mixture of 4-nitrophenyl alpha-L-fucopyranoside and D-mannopyranose, 3-O-alpha-L-fucopyranosyl-D-mannopyranose was synthesised through the transferring action of alpha-fucosidase (Sumizyme PHY). 6(I), 6(IV)-Di-O-(3-O-alpha-L-fucopyranosyl-alpha-D-mannopyranosyl)-cyclomaltoheptaose 8, 6(I), 6(IV)-di-O-[alpha-L-Fuc(1 -> 3)-alpha-D-Man]-beta CD} was chemically synthesised using the trichloroacetimidate method. The structures were confirmed by MS and NMR spectroscopy. A cell-based assay using the fucosyl beta CD derivatives, including the newly synthesised 8, showed that derivatives with two branches of the alpha-L-Fuc or alpha-L-Fuc(1 -> 3)-alpha-D-Man residues possessed slight growth-promoting effects and lower toxicity in HCT116 cells compared to those with one branch. These compounds may be useful as drug carriers in targeted drug delivery systems. (C) 2013 Elsevier Ltd. All rights reserved.