6-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid (2-amino-ethyl)-amide | 219791-80-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid (2-amino-ethyl)-amide
• 英文别名: N-(2-aminoethyl)-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanamide
• CAS: 219791-80-7
• 化学式: C₁₄H₂₈N₂O₇
• 分子量: 336.386
• InChiKey: GSJCRSUXXFIRKL-RGCYKPLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  155
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  方酸二乙酯 、 6-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid (2-amino-ethyl)-amide 以 乙醇 为溶剂， 反应 6.0h， 以78%的产率得到N-[2-[(2-ethoxy-3,4-dioxocyclobuten-1-yl)amino]ethyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanamide
  参考文献：
  名称：

  Studies towards neoglycoconjugates from the monosaccharide determinant of Vibrio cholerae O:1, serotype Ogawa using the diethyl squarate reagent

  摘要：

  The effect of reaction time, concentration and molar excess of hapten upon the efficiency of the conjugation of carbohydrates to proteins using the diethyl squarate reagent has been studied using chicken serum albumin (CSA) as the carrier protein and a linker-equipped D-glucose derivative as the hapten. A high degree of incorporation of the latter into CSA was achieved with high efficiency, and the use of a large excess of the ligand was not necessary. Conjugation of the immunodominant monosaccharide determinant of Vibrio cholerae O:1, serotype Ogawa, bearing the same spacer, followed a similar pattern, showing that the nature of the carbohydrate does not substantially affect the outcome of the conjugation and that a predicted degree of antigen-loading onto carrier protein is possible to achieve. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00261-4
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 在 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 甲苯 为溶剂， 反应 60.0h， 生成 6-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid (2-amino-ethyl)-amide
  参考文献：
  名称：

  Studies towards neoglycoconjugates from the monosaccharide determinant of Vibrio cholerae O:1, serotype Ogawa using the diethyl squarate reagent

  摘要：

  The effect of reaction time, concentration and molar excess of hapten upon the efficiency of the conjugation of carbohydrates to proteins using the diethyl squarate reagent has been studied using chicken serum albumin (CSA) as the carrier protein and a linker-equipped D-glucose derivative as the hapten. A high degree of incorporation of the latter into CSA was achieved with high efficiency, and the use of a large excess of the ligand was not necessary. Conjugation of the immunodominant monosaccharide determinant of Vibrio cholerae O:1, serotype Ogawa, bearing the same spacer, followed a similar pattern, showing that the nature of the carbohydrate does not substantially affect the outcome of the conjugation and that a predicted degree of antigen-loading onto carrier protein is possible to achieve. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00261-4