[(2R,3S,4R,5R,6S)-5-azido-3-hydroxy-4-phenylmethoxy-6-phenylsulfanyloxan-2-yl]methyl methanesulfonate | 1245566-82-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4R,5R,6S)-5-azido-3-hydroxy-4-phenylmethoxy-6-phenylsulfanyloxan-2-yl]methyl methanesulfonate
• CAS: 1245566-82-8
• 化学式: C₂₀H₂₃N₃O₆S₂
• 分子量: 465.551
• InChiKey: OLZFCKBIEMZVOB-WAPOTWQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R,6S)-5-azido-3-hydroxy-4-phenylmethoxy-6-phenylsulfanyloxan-2-yl]methyl methanesulfonate 在 吡啶 、 盐酸 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 5%-palladium/activated carbon 、 氢气 、 一水合肼 、 乙酰氯 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 68.02h， 生成 methyl (2,6-diamino-2,6-dideoxy-α-D-glucopyranosyl)-(1->4)-2,6-diamino-2,6-dideoxy-α-D-glucopyranoside tetrahydrochloride
  参考文献：
  名称：

  Synthesis of Oligodiaminosaccharides Having α-Glycoside Bonds and Their Interactions with Oligonucleotide Duplexes

  摘要：

  Syntheses of the novel oligodiaminosaccharides, alpha-(1 -> 4)linked-2,6-diamino-2,6-dideoxy-D-glucopyranose oligomers, and their interactions with nucleic acid duplexes DNA-DNA, RNA-RNA, and DNA-RNA are described. Monomers to tetramers of oligodiaminoglucose derivatives having alpha-glycosyl bonds were successfully synthesized using a chain elongation cycle including glycosylation reactions of a 6-phthalimide glycosyl donor. UV melting experiments for a variety of nucleic acid duplexes in the absence and presence of the oligodiaminosaccharides were performed. The synthesized oligodiaminosaccharides exhibited notable thermodynamic stabilization effects on A-type RNA-RNA and DNA-RNA duplexes, whereas B-type DNA-DNA duplexes were not stabilized by the synthesized oligodiaminosaccharides. Among the oligodiaminosaccharides, the tetramer exhibited the highest ability to stabilize A-type duplexes, and the increase in T(m) values induced by the tetramer were higher than those induced by neomycin B and tobramycin, which are known aminoglycosides having ability to bind and stabilize a variety of RNA molecules. CD spectrometry experiments revealed that the oligodiaminosaccharides caused small structural changes in RNA-RNA duplexes, whereas no appreciable changes were observed in the structure of DNA-DNA duplexes. ITC (isothermal titration calorimetry) experiments demonstrated that the amount of heat generated by the interaction between RNA-RNA duplexes and the tetradiaminosaccharides was approximately double that generated by that between DNA-DNA duplexes and the tetradiaminosaccharides. These results strongly suggested the existence of an A-type nucleic acid specific-binding mode of the oligodiaminosaccharides, which bind to these duplexes and cause small structural changes.

  DOI：

  10.1021/jo200951p
• 作为产物：
  描述：

  甲基磺酰氯 、 phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 在 吡啶 作用下， 反应 5.0h， 生成 [(2R,3S,4R,5R,6S)-5-azido-3-hydroxy-4-phenylmethoxy-6-phenylsulfanyloxan-2-yl]methyl methanesulfonate
  参考文献：
  名称：

  Oligo-Aminosaccharide compound

  摘要：

  由3到6个糖苷结合形成的寡糖氨基酸化合物，例如2,6-二氨基-2,6-二去氧-α-(1→4)-D-葡萄糖吡喃糖寡聚体，或其盐，具有高亲和力双链核酸。

  公开号：

  US20110003980A1

文献信息

• Oligo-Aminosaccharide compound
  申请人：Wada Takeshi

  公开号：US20110003980A1

  公开（公告）日：2011-01-06

  An oligo-aminosaccharide compound formed by binding 3 to 6 saccharides, such as 2,6-diamino-2,6-dideoxy-α-(1→4)-D-glucopyranose oligomers, or a salt thereof, which has high affinity to a double-stranded nucleic acid.

  由3到6个糖苷结合形成的寡糖氨基酸化合物，例如2,6-二氨基-2,6-二去氧-α-(1→4)-D-葡萄糖吡喃糖寡聚体，或其盐，具有高亲和力双链核酸。
• Synthesis of Oligodiaminosaccharides Having α-Glycoside Bonds and Their Interactions with Oligonucleotide Duplexes
  作者：Rintaro Iwata、Masafumi Sudo、Kenta Nagafuji、Takeshi Wada

  DOI：10.1021/jo200951p

  日期：2011.8.5

  Syntheses of the novel oligodiaminosaccharides, alpha-(1 -> 4)linked-2,6-diamino-2,6-dideoxy-D-glucopyranose oligomers, and their interactions with nucleic acid duplexes DNA-DNA, RNA-RNA, and DNA-RNA are described. Monomers to tetramers of oligodiaminoglucose derivatives having alpha-glycosyl bonds were successfully synthesized using a chain elongation cycle including glycosylation reactions of a 6-phthalimide glycosyl donor. UV melting experiments for a variety of nucleic acid duplexes in the absence and presence of the oligodiaminosaccharides were performed. The synthesized oligodiaminosaccharides exhibited notable thermodynamic stabilization effects on A-type RNA-RNA and DNA-RNA duplexes, whereas B-type DNA-DNA duplexes were not stabilized by the synthesized oligodiaminosaccharides. Among the oligodiaminosaccharides, the tetramer exhibited the highest ability to stabilize A-type duplexes, and the increase in T(m) values induced by the tetramer were higher than those induced by neomycin B and tobramycin, which are known aminoglycosides having ability to bind and stabilize a variety of RNA molecules. CD spectrometry experiments revealed that the oligodiaminosaccharides caused small structural changes in RNA-RNA duplexes, whereas no appreciable changes were observed in the structure of DNA-DNA duplexes. ITC (isothermal titration calorimetry) experiments demonstrated that the amount of heat generated by the interaction between RNA-RNA duplexes and the tetradiaminosaccharides was approximately double that generated by that between DNA-DNA duplexes and the tetradiaminosaccharides. These results strongly suggested the existence of an A-type nucleic acid specific-binding mode of the oligodiaminosaccharides, which bind to these duplexes and cause small structural changes.