6-(2,3,4,6-tetra-O-(2-propenyl)-β-D-galactopyranosylamino)-6-oxohexanoic acid benzyl ester | 873576-79-5

• 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-(2,3,4,6-tetra-O-(2-propenyl)-β-D-galactopyranosylamino)-6-oxohexanoic acid benzyl ester
• 英文别名: 6-[2,3,4,6-tetra-O-(2-propenyl)-β-D-galactopyranosylamino]-6-oxohexanoic acid benzyl ester
• CAS: 873576-79-5
• 化学式: C₃₁H₄₃NO₈
• 分子量: 557.684
• InChiKey: PARFNVILBPMFQT-PLZPULBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  40.0
• 可旋转键数：
  21.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  101.55
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-(2,3,4,6-tetra-O-(2-propenyl)-β-D-galactopyranosylamino)-6-oxohexanoic acid benzyl ester 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 4.0h， 生成 6-(2,3,4,6-tetra-O-{3-[2-(tert-butoxycarbonylamino)ethylthio]propyl}-β-D-galactopyranosylamino)-6-oxohexanoic acid
  参考文献：
  名称：

  Polycationic lipophilic-core dendrons as penetration enhancers for the oral administration of low molecular weight heparin

  摘要：

  Two polycationic lipophilic-core carbohydrate-based dendrons 2a-b and five polycationic lipophilic-core peptide dendrons 3-6, containing four arginine or lysine terminal residues, were synthesized and then tested in rats as penetration enhancers for the oral delivery of low molecular weight heparin. Better results were obtained with dendrons containing terminal lysine residues than terminal arginine. A significant anti-factor Xa activity was obtained when low molecular weight heparin was coadministered with dendron 5. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.004
• 作为产物：
  描述：

  1-叠氮-1-脱氧-β-D-吡喃半乳糖苷 在 水 、 sodium hydride 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 6-(2,3,4,6-tetra-O-(2-propenyl)-β-D-galactopyranosylamino)-6-oxohexanoic acid benzyl ester
  参考文献：
  名称：

  Polycationic lipophilic-core dendrons as penetration enhancers for the oral administration of low molecular weight heparin

  摘要：

  Two polycationic lipophilic-core carbohydrate-based dendrons 2a-b and five polycationic lipophilic-core peptide dendrons 3-6, containing four arginine or lysine terminal residues, were synthesized and then tested in rats as penetration enhancers for the oral delivery of low molecular weight heparin. Better results were obtained with dendrons containing terminal lysine residues than terminal arginine. A significant anti-factor Xa activity was obtained when low molecular weight heparin was coadministered with dendron 5. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.004

文献信息

• Design and Synthesis of Lipopeptide - Carbohydrate Assembled Multivalent Vaccine Candidates Using Native Chemical Ligation
  作者：Wei Zhong、Mariusz Skwarczynski、Yoshio Fujita、Pavla Simerska、Michael F. Good、Istvan Toth

  DOI：10.1071/ch09065

  日期：——

  attached peptides to form a well defined tertiary structure. For self-adjuvanting human vaccines, the conjugation of immunostimulatory lipids has been demonstrated as a potentially safe method. This study describes the design and optimized synthesis of two lipopeptide conjugated carbohydrate templates and the assembling of peptide antigens. These lipopeptide–carbohydrate assembled multivalent vaccine candidates

  由于主要毒力因子M蛋白诱导自身免疫，针对A组链球菌感染的合成疫苗的开发越来越重要。然而，肽疫苗通常免疫原性差，需要与载体和佐剂一起给药。递送抗原性肽的有前途的方法之一是在合适的模板上组装肽，该模板指导附着的肽形成定义明确的三级结构。对于自佐剂人类疫苗，免疫刺激脂质的缀合已被证明是一种潜在的安全方法。这项研究描述了两个脂肽缀合的碳水化合物模板的设计和优化合成以及肽抗原的组装。当应用天然化学连接时，这些脂肽-碳水化合物组装的多价疫苗候选物以高产率和高纯度获得。圆二色性研究表明，模板组装的肽形成四个α-螺旋束。开发的技术扩展了碳水化合物模板和脂肽缀合物在生产自佐剂和拓扑控制候选疫苗中的用途。