5-(methoxycarbonyl) pentyl β-d-glucopyranoside | 219791-75-0

• 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: 5-(methoxycarbonyl) pentyl β-d-glucopyranoside
• 英文别名: 6-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid methyl ester；methyl 6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoate
• CAS: 219791-75-0
• 化学式: C₁₃H₂₄O₈
• 分子量: 308.329
• InChiKey: IYTWFACKZFMVIU-KABOQKQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(methoxycarbonyl) pentyl β-d-glucopyranoside 以 乙醇 为溶剂， 反应 36.0h， 生成 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：

  5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 生成 5-(methoxycarbonyl) pentyl β-d-glucopyranoside
  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

文献信息

• Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold
  作者：Vincent Fagan、Istvan Toth、Pavla Simerska

  DOI：10.3762/bjoc.10.181

  日期：——

  A novel convergent synthetic strategy for the construction of multicomponent self-adjuvanting lipopeptide vaccines was developed. A tetraalkyne-functionalized glucose derivative and lipidated Fmoc-lysine were prepared by novel efficient and convenient syntheses. The carbohydrate building block was coupled to the self-adjuvanting lipidic moiety (three lipidated Fmoc-lysines) on solid support. Four copies of a group A streptococcal B cell epitope (J8) were then conjugated to the glyco-lipopeptide using a copper-catalyzed cycloaddition reaction. The approach was elaborated by the preparation of a second vaccine candidate which incorporated an additional promiscuous T-helper epitope.

  开发了一种新的汇聚合成策略，用于构建多成分自免疫脂肽疫苗。通过新的高效便捷的合成方法制备了四炔基功能葡萄糖衍生物和脂化Fmoc-赖氨酸。将碳水化合物构建块与自免疫脂质基团（三个脂化Fmoc-赖氨酸）在固相支持上偶联。然后，使用铜催化环加成反应将四个A型链球菌B细胞表位（J8）的拷贝连接到糖脂肽上。该方法通过准备第二个疫苗候选者来详细说明，该候选者包含一个额外的杂交T细胞表位。