(2R)-2,3-bis[(3R,7R,11R)-3,7,11,15-tetramethylhexadecyloxy]propan-1-yl 4-O-(2,3,4,6-tetra-O-α-D-glucopyranosyl)-4-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 952042-69-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R)-2,3-bis[(3R,7R,11R)-3,7,11,15-tetramethylhexadecyloxy]propan-1-yl 4-O-(2,3,4,6-tetra-O-α-D-glucopyranosyl)-4-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 952042-69-2
• 化学式: C₈₁H₁₃₈O₂₈
• 分子量: 1559.97
• InChiKey: MNLRWAJMOVVXMQ-ICFBQMEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.49
• 重原子数：
  109.0
• 可旋转键数：
  53.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  336.84
• 氢给体数：
  0.0
• 氢受体数：
  28.0

反应信息

• 作为反应物：
  描述：

  (2R)-2,3-bis[(3R,7R,11R)-3,7,11,15-tetramethylhexadecyloxy]propan-1-yl 4-O-(2,3,4,6-tetra-O-α-D-glucopyranosyl)-4-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以90%的产率得到(2R)-2,3-bis[(3R,7R,11R)-3,7,11,15-tetramethylhexadecyloxy]propan-1-yl 4-O-(α-D-glucopyranosyl)-4-O-(α-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of archaeal glycolipid adjuvants—what is the optimum number of sugars?

  摘要：

  As part of a programme to optimize the use of archaeal-lipid liposomes (archaeosomes) as vaccine adjuvants, we present the synthesis and immunological testing of an oligomeric series of mannose glycolipids (Manp(1-5)). To generate the parent archaeol alcohol precursor, the polar lipids extracted from the archaeon Halobacterium salinarum were hydrolyzed to remove polar head groups, and the archaeol so generated partitioned into diethyl ether. This alcohol was then iteratively glycosylated with the donor 2-O-acetyl-3,4,6-tri-O-benzyl-alpha/beta-D-mannopyranosyl trichloroacetimidate to yield alpha-Manp-(1-->2) oligomers. A starch-derived trimer was also synthesized as a control. To promote hydration and form stable archaeosomes, an archaeal anionic lipid archaetidylglycerol (AG) was included in a 4:1 molar ratio. Archaeosomes prepared from Manp(1-2)-AG were recovered at only 34-37%, whereas Manp(3-4)-AG recoveries were 72-77%. Lipid recovery following hydration of Manp(5)-AG archaeosomes declined to 34%, indicating an optimum of 3-4 Manp units for bilayer formation. The CD8(+) T cell response in mice immunized with Manp(3-5) archaeosomes containing ovalbumin was highest for Manp(4) and declined for Manp(3) and Manp(5), revealing an optimum length of four unbranched units. The starch-derived trimer was more active than the Manp oligomers, suggesting the involvement of either a general binding lectin on antigen-presenting cells with highest affinity for triglucose or multiple lectin receptors. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.06.021
• 作为产物：
  描述：

  2,3-bis-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecan-1-yl]-sn-glycerol 、 4-O-(4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetylα-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α/β-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 以53%的产率得到(2R)-2,3-bis[(3R,7R,11R)-3,7,11,15-tetramethylhexadecyloxy]propan-1-yl 4-O-(2,3,4,6-tetra-O-α-D-glucopyranosyl)-4-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of archaeal glycolipid adjuvants—what is the optimum number of sugars?

  摘要：

  As part of a programme to optimize the use of archaeal-lipid liposomes (archaeosomes) as vaccine adjuvants, we present the synthesis and immunological testing of an oligomeric series of mannose glycolipids (Manp(1-5)). To generate the parent archaeol alcohol precursor, the polar lipids extracted from the archaeon Halobacterium salinarum were hydrolyzed to remove polar head groups, and the archaeol so generated partitioned into diethyl ether. This alcohol was then iteratively glycosylated with the donor 2-O-acetyl-3,4,6-tri-O-benzyl-alpha/beta-D-mannopyranosyl trichloroacetimidate to yield alpha-Manp-(1-->2) oligomers. A starch-derived trimer was also synthesized as a control. To promote hydration and form stable archaeosomes, an archaeal anionic lipid archaetidylglycerol (AG) was included in a 4:1 molar ratio. Archaeosomes prepared from Manp(1-2)-AG were recovered at only 34-37%, whereas Manp(3-4)-AG recoveries were 72-77%. Lipid recovery following hydration of Manp(5)-AG archaeosomes declined to 34%, indicating an optimum of 3-4 Manp units for bilayer formation. The CD8(+) T cell response in mice immunized with Manp(3-5) archaeosomes containing ovalbumin was highest for Manp(4) and declined for Manp(3) and Manp(5), revealing an optimum length of four unbranched units. The starch-derived trimer was more active than the Manp oligomers, suggesting the involvement of either a general binding lectin on antigen-presenting cells with highest affinity for triglucose or multiple lectin receptors. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.06.021