(2R,4S,5R,6R)-2,4-dihydroxy-5-(3,3,3-trifluoropropanamido)-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid | 765302-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5R,6R)-2,4-dihydroxy-5-(3,3,3-trifluoropropanamido)-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid
• CAS: 765302-27-0
• 化学式: C₁₂H₁₈F₃NO₉
• 分子量: 377.271
• InChiKey: YWTSVXZQWLKGFR-VTERZIIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.94
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  176.78
• 氢给体数：
  7.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,2-二氨基-4,5-亚甲基二氧基苯双盐酸盐 、 (2R,4S,5R,6R)-2,4-dihydroxy-5-(3,3,3-trifluoropropanamido)-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid 生成
  参考文献：
  名称：

  Fluorination of mammalian cell surfaces via the sialic acid biosynthetic pathway

  摘要：

  Metabolic oligosaccharide engineering has been employed to introduce fluorine-containing groups onto mammalian cell surfaces. Incubation of HeLa, Jurkat, and HL60 cells in culture with fluorinated sialic acid and mannosamine analogues resulted in cell-surface presentation of fluorinated glycans. Metabolic conversion of fluorinated precursors was detected and quantified by DMB-derivatization and HPLC ESI-MS analysis. Between 7% and 72% of total membrane-associated sialosides were fluorinated, depending on the precursor used and the cell type. Fluorination of mammalian cell surfaces provides a means for introducing a bioorthogonal surface for modulating noncovalent interactions such as those involved in cell adhesion. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.010
• 作为产物：
  描述：

  sodium pyruvate 、 在 sodium azide 、 sialic acid aldolase 、 1,4-Dithioerythritol 作用下， 反应 72.0h， 生成 (2R,4S,5R,6R)-2,4-dihydroxy-5-(3,3,3-trifluoropropanamido)-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid
  参考文献：
  名称：

  Fluorination of mammalian cell surfaces via the sialic acid biosynthetic pathway

  摘要：

  Metabolic oligosaccharide engineering has been employed to introduce fluorine-containing groups onto mammalian cell surfaces. Incubation of HeLa, Jurkat, and HL60 cells in culture with fluorinated sialic acid and mannosamine analogues resulted in cell-surface presentation of fluorinated glycans. Metabolic conversion of fluorinated precursors was detected and quantified by DMB-derivatization and HPLC ESI-MS analysis. Between 7% and 72% of total membrane-associated sialosides were fluorinated, depending on the precursor used and the cell type. Fluorination of mammalian cell surfaces provides a means for introducing a bioorthogonal surface for modulating noncovalent interactions such as those involved in cell adhesion. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.010