benzyl [(2-deoxy-2-acetamido-β-D-glucopyranosyl)]-(1->6)-[(4-deoxy-4-fluoro-β-D-galactopyranosyl)]-(1->3)-2-deoxy-2-acetamido-α-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl [(2-deoxy-2-acetamido-β-D-glucopyranosyl)]-(1->6)-[(4-deoxy-4-fluoro-β-D-galactopyranosyl)]-(1->3)-2-deoxy-2-acetamido-α-D-galactopyranoside
• 英文别名: Gal4F(b1-3)[GlcNAc(b1-6)]GalNAc(a)-O-Bn；N-[(2R,3R,4R,5S,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-4-[(2R,3R,4R,5R,6R)-5-fluoro-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-6-phenylmethoxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₂₉H₄₃FN₂O₁₅
• 分子量: 678.663
• InChiKey: ABBQXNJVEGAYFV-BITSEOLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  255
• 氢给体数：
  9
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-α-D-galactopyranosyl bromide 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 sodium methylate 、 氰化汞 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 硝基甲烷 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 45.0h， 生成 benzyl [(2-deoxy-2-acetamido-β-D-glucopyranosyl)]-(1->6)-[(4-deoxy-4-fluoro-β-D-galactopyranosyl)]-(1->3)-2-deoxy-2-acetamido-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Fluorinated Mucin Core 2 Branched Oligosaccharides with the Potential of Novel Substrates and Enzyme Inhibitors for Glycosyltransferases and Sulfotransferases

  摘要：

  Syntheses of fluorinated mucin core 2 tri- and tetrasaccharides modified at the C-3 or C-4 position of the pertinent galactose residue are reported. These compounds were used for the study of sialyltransferases and 3-O-sulfotransferases involved in the biosynthesis of O-glycans. Our acceptor substrate specificity studies on three cloned sialyltransferases (Sia-Ts) revealed that a 3- or 4-fluoro substituent in, beta 1,4Gal resulted in poor acceptors for alpha 2,6(N)Sia-T and alpha 2,3(N)Sia-T, whereas 4-fluoro-Gal,beta 1,3GalNAc alpha was a good acceptor for alpha 2,3(O)Sia-T. Uniquely, 4-F-Gal,beta 1,4GlcNAc,beta 1,6(Gal,beta 1,3)GalNAc alpha-OBn was an inhibitor of alpha 2,6(N)Sia-T activity but not alpha 2,3(N)Sia-T activity. Further we found that the activities of only Gal 3-O-sulfotransferases and not sialyltransferases were adversely affected by a C-3 fluoro substituent at the other Gal terminal of mucin core 2. The strategy of building branched mucin core 2 structures by three glycosidation sequence coupling three classes of glycosyl donors with the reactivity-matching acceptors proved to be successful in syntheses of modified mucin-type core structures of O-glycan. The relative poor yields of the glycosylations using fluorinated galactosyl donors indicated that the fluorine modification dramatically decreased the donor reactivity due to electron-withdrawing effect.

  DOI：

  10.1021/jo052626j