3-O-benzyl-α⁴,α⁵-di-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-6-fluoropyridoxol | 882979-66-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-O-benzyl-α⁴,α⁵-di-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-6-fluoropyridoxol
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[[2-fluoro-6-methyl-5-phenylmethoxy-3-[[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxymethyl]pyridin-4-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 882979-66-0
• 化学式: C₄₃H₅₂FNO₂₁
• 分子量: 937.878
• InChiKey: RAOQKAABVXCEFM-WXBZIBSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  66
• 可旋转键数：
  27
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  269
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-α⁴,α⁵-di-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-6-fluoropyridoxol 在 palladium on activated charcoal 4 A molecular sieve 、 氨 、 氢气 、 氰化汞 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、172.37 kPa 条件下， 反应 36.0h， 生成 3-O-(β-D-galactopyranosyl)-α⁴,α⁵-di-O-(β-D-mannopyranosyl)-6-fluoropyridoxol
  参考文献：
  名称：

  Synthesis and Characterization of Novel lacZ Gene Reporter Molecules:  Detection of β-Galactosidase Activity by ¹⁹F Nuclear Magnetic Resonance of Polyglycosylated Fluorinated Vitamin B₆

  摘要：

  Gene therapy has emerged as a promising strategy for treatment of various diseases. However, widespread implementation is hampered by difficulties in assessing the success of transfection, in particular, the spatial extent of expression in the target tissue and the longevity of expression. Thus, the development of noninvasive reporter techniques based on appropriate molecules and imaging modalities may help to assay gene expression. We have previously demonstrated the ability to detect beta-galactosidase (beta-gal) activity on the basis of F-19 NMR chemical shift associated with release of fluorophenyl aglycons from galactopyranoside conjugates. Use of fluoropyridoxol as the aglycon provides a potential less toxic alternative and we now report the design, synthesis, and structural analysis of a series of novel polyglycosylated fluorinated vitamin 136 derivatives as F-19 NMR-sensitive aglycons for detection of lacZ gene expression. In particular, we report the activity of 3,alpha(4),alpha(5)-tri-O-(beta-D-galactopyranosyl)-6-fluoropyridoxol 4, 3-O-(beta-D-galactopyranosyl)-alpha(4),alpha(5)-di-O-(beta-D-glucopyranosyl)-6-fluoropyridoxol 12, and 3-O-(beta-D-galactopyranosyl)-alpha(4),alpha(5)-di-O-(alpha-D-mannopyranosyl)-6-fluoropyridoxol 13. Compounds 4, 12, and 13 all show promising characteristics including highly sensitive F-19 NMR response to beta-gal activity (Delta delta = 9.0 similar to 9.4 ppm), minimal toxicity for substrate or aglycon, and good water solubility. However, the differential glycosylation of 12 and 13 appears more advantageous for assessing lacZ gene expression in vivo.

  DOI：

  10.1021/jm051049o
• 作为产物：
  描述：

  6-fluoropyridoxol 在 4 A molecular sieve 、 四丁基溴化铵 、 氰化汞 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 3-O-benzyl-α⁴,α⁵-di-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-6-fluoropyridoxol
  参考文献：
  名称：

  Synthesis and Characterization of Novel lacZ Gene Reporter Molecules:  Detection of β-Galactosidase Activity by ¹⁹F Nuclear Magnetic Resonance of Polyglycosylated Fluorinated Vitamin B₆

  摘要：

  Gene therapy has emerged as a promising strategy for treatment of various diseases. However, widespread implementation is hampered by difficulties in assessing the success of transfection, in particular, the spatial extent of expression in the target tissue and the longevity of expression. Thus, the development of noninvasive reporter techniques based on appropriate molecules and imaging modalities may help to assay gene expression. We have previously demonstrated the ability to detect beta-galactosidase (beta-gal) activity on the basis of F-19 NMR chemical shift associated with release of fluorophenyl aglycons from galactopyranoside conjugates. Use of fluoropyridoxol as the aglycon provides a potential less toxic alternative and we now report the design, synthesis, and structural analysis of a series of novel polyglycosylated fluorinated vitamin 136 derivatives as F-19 NMR-sensitive aglycons for detection of lacZ gene expression. In particular, we report the activity of 3,alpha(4),alpha(5)-tri-O-(beta-D-galactopyranosyl)-6-fluoropyridoxol 4, 3-O-(beta-D-galactopyranosyl)-alpha(4),alpha(5)-di-O-(beta-D-glucopyranosyl)-6-fluoropyridoxol 12, and 3-O-(beta-D-galactopyranosyl)-alpha(4),alpha(5)-di-O-(alpha-D-mannopyranosyl)-6-fluoropyridoxol 13. Compounds 4, 12, and 13 all show promising characteristics including highly sensitive F-19 NMR response to beta-gal activity (Delta delta = 9.0 similar to 9.4 ppm), minimal toxicity for substrate or aglycon, and good water solubility. However, the differential glycosylation of 12 and 13 appears more advantageous for assessing lacZ gene expression in vivo.

  DOI：

  10.1021/jm051049o