6-O-(α-L-fucopyranosyl)-βCD | 1186219-77-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(α-L-fucopyranosyl)-βCD
• 英文别名: (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,30,35-hexakis(hydroxymethyl)-25-[[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
• CAS: 1186219-77-1
• 化学式: C₄₈H₈₀O₃₉
• 分子量: 1281.14
• InChiKey: LFHPDCDHQKBOMV-QVVMJBFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -16.1
• 重原子数：
  87
• 可旋转键数：
  9
• 环数：
  22.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  613
• 氢给体数：
  23
• 氢受体数：
  39

反应信息

• 作为产物：
  描述：

  [(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36S,37R,38S,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecaacetyloxy-15,20,25,30-tetrakis(acetyloxymethyl)-10,35-bis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methyl acetate 、 O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 甲酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 3.0h， 生成 6(1),6(3)-di-O-(β-L-fucopyranosyl)-βCD 、 6-O-(α-l-Fuc)-β-CD 、 6-O-(α-L-fucopyranosyl)-βCD 、 6(1),6(3)-di-O-(α-L-fucopyranosyl)-βCD
  参考文献：
  名称：

  Preparation and Characterization of Branched β-Cyclodextrins Having α-L-Fucopyranose and a Study of Their Functions

  摘要：

  利用相应的真品化合物，化学合成了 61,6n-di-O-(α-l-岩藻酰)-β-环糊精[61,6n-di-O-(α-l-Fuc)-βCD，n=2-4]的三种位置异构体、61,6n-二-O-(叔丁基二甲基硅烷基)-βCD（n=2-4）作为岩藻糖基受体，2,3,4-三-O-苄基-l-呋喃糖基三氯乙酰亚胺作为岩藻糖基供体。通过高效液相色谱、质谱和核磁共振光谱分析了它们的结构。α-l-Fuc-βCDs的溶血活性低于βCD，而这些支链βCDs的水溶性远高于βCD。利用基于表面等离子体共振（SPR）技术的光学生物传感器研究了这些化合物与岩藻糖结合凝集素（AAL）之间的分子相互作用。作为岩藻糖结合位置函数的结合亲和力顺序为 61,64- > 61,63- > 61,62-di-O-(α-l-Fuc)-βCD > 6-O-(α-l-Fuc)-βCD。

  DOI：

  10.1271/bbb.80609

文献信息

• Preparation and Characterization of Branched β-Cyclodextrins Having α-<scp>L</scp>-Fucopyranose and a Study of Their Functions
  作者：Yuki NISHI、Toshiko TANIMOTO

  DOI：10.1271/bbb.80609

  日期：2009.3.23

  Three positional isomers of 61,6n-di-O-(α-l-fucopyranosyl)-β-cyclodextrin [61,6n-di-O-(α-l-Fuc)-βCD, n=2–4] were chemically synthesized by using the corresponding authentic compounds, 61,6n-di-O-(tert-butyldimethylsilyl)-βCD (n=2–4) as fucosyl acceptors and 2,3,4-tri-O-benzyl-l-fucopyranosyl trichloroacetimidate as a fucosyl donor. Their structures were analyzed by HPLC, MS and NMR spectroscopy. The hemolytic activities of the α-l-Fuc-βCDs were lower than that of βCD, while the water solubility of these branched βCDs was much higher than that of βCD. The molecular interaction between these compounds and the fucose-binding lectin, Aleuria aurantia lectin (AAL), was investigated by using an optical biosensor based on the surface plasmon resonance (SPR) technique. The order of binding affinity, as a function of the fucose-binding position, was 61,64- > 61,63- > 61,62-di-O-(α-l-Fuc)-βCD > 6-O-(α-l-Fuc)-βCD.

  利用相应的真品化合物，化学合成了 61,6n-di-O-(α-l-岩藻酰)-β-环糊精[61,6n-di-O-(α-l-Fuc)-βCD，n=2-4]的三种位置异构体、61,6n-二-O-(叔丁基二甲基硅烷基)-βCD（n=2-4）作为岩藻糖基受体，2,3,4-三-O-苄基-l-呋喃糖基三氯乙酰亚胺作为岩藻糖基供体。通过高效液相色谱、质谱和核磁共振光谱分析了它们的结构。α-l-Fuc-βCDs的溶血活性低于βCD，而这些支链βCDs的水溶性远高于βCD。利用基于表面等离子体共振（SPR）技术的光学生物传感器研究了这些化合物与岩藻糖结合凝集素（AAL）之间的分子相互作用。作为岩藻糖结合位置函数的结合亲和力顺序为 61,64- > 61,63- > 61,62-di-O-(α-l-Fuc)-βCD > 6-O-(α-l-Fuc)-βCD。