benzyl [(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)]-(1->6)-3-[4-(2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)]-2-deoxy-2-acetamido-α-D-galactopyranoside | 890016-25-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl [(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)]-(1->6)-3-[4-(2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)]-2-deoxy-2-acetamido-α-D-galactopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-6-[[(2R,3R,4R,5R,6S)-5-acetamido-4-[(2R,3R,4R,5S,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-fluorooxan-2-yl]oxy-3-hydroxy-6-phenylmethoxyoxan-2-yl]methoxy]-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl acetate
• CAS: 890016-25-8
• 化学式: C₄₇H₅₅FN₂O₂₂
• 分子量: 1018.95
• InChiKey: NCHWMEYHCJHFGM-JTTUJZQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  72
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  300
• 氢给体数：
  2
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  benzyl [(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)]-(1->6)-3-[4-(2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)]-2-deoxy-2-acetamido-α-D-galactopyranoside 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成
  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
• 作为产物：
  描述：

  methyl-2,3,6-tri-O-acetyl-4-fluoride-β-D-galactoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 硫酸 、 氢溴酸 、 氰化汞 、 乙酸酐 、 溶剂黄146 作用下， 以 硝基甲烷 、 二氯甲烷 、 苯 为溶剂， 反应 19.5h， 生成 benzyl [(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)]-(1->6)-3-[4-(2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)]-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