3-O-benzyl-2-O-((R)-10-methyloctadecanoyl)-1-O-palmitoyl-sn-glycerol | 935852-33-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 3-O-benzyl-2-O-((R)-10-methyloctadecanoyl)-1-O-palmitoyl-sn-glycerol
• 英文别名: [(2S)-1-hexadecanoyloxy-3-phenylmethoxypropan-2-yl] (10R)-10-methyloctadecanoate
• CAS: 935852-33-8
• 化学式: C₄₅H₈₀O₅
• 分子量: 701.127
• InChiKey: IRJNESFJAIAVED-VROXBXNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.4
• 重原子数：
  50
• 可旋转键数：
  39
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-2-O-((R)-10-methyloctadecanoyl)-1-O-palmitoyl-sn-glycerol 在 palladium on activated charcoal 四氮唑 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 benzyl (2-O-(R)-10-methyloctadecanoyl-1-O-hexadecanoyl-sn-glycero)-diisopropylphosphoramidite
  参考文献：
  名称：

  Synthesis and Structure of Phosphatidylinositol Dimannoside

  摘要：

  (R)-Tuberculostearic acid (2) was synthesized in seven steps from (S)-citronellol (5). The carbon chain of 2 was assembled by copper-catalyzed cross coupling of (S)-citronellol tosylate (6) and hexylmagnesium bromide; subsequent ozonolysis and reaction with 6-benzyloxyhexylmagnesium bromide furnished alcohol 10. Functional group manipulation afforded (R)-2 in 49% overall yield from 5. DCC coupling of (R)-2 with 3-O-benzyl-1-O-palmitoyl-sn-glycerol (16), followed by hydrogenolytic removal of the benzyl group and treatment with benzyl bis(diisopropyl)phosphoramidite, afforded phosphoramidite 20. Tetrazole-mediated coupling of 20 with PIM1 head group 21 gave 22, and subsequent debenzylation afforded phosphatidylinositol mono-mannoside, PIM1 (23). Similarly, coupling of 20 and 24 and removal of the benzyl protecting groups gave PIM2 (1c). Both 23 and 1c have a clearly defined acylation pattern, which was confirmed by mass spectrometry, with sn-1 palmitoyl and sn-2 tuberculostearoyl groups on the glycerol moiety. Both 23 and 1c were shown to modulate the release of the pro-inflammatory cytokine, IL-12, in a dendritic cell assay.

  DOI：

  10.1021/jo0625599
• 作为产物：
  描述：

  magnesium,hexoxymethylbenzene,bromide 在 吡啶 、 4-二甲氨基吡啶 、 aluminum oxide 、 potassium permanganate 、 四丁基溴化铵 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 181.0h， 生成 3-O-benzyl-2-O-((R)-10-methyloctadecanoyl)-1-O-palmitoyl-sn-glycerol
  参考文献：
  名称：

  Synthesis and Structure of Phosphatidylinositol Dimannoside

  摘要：

  (R)-Tuberculostearic acid (2) was synthesized in seven steps from (S)-citronellol (5). The carbon chain of 2 was assembled by copper-catalyzed cross coupling of (S)-citronellol tosylate (6) and hexylmagnesium bromide; subsequent ozonolysis and reaction with 6-benzyloxyhexylmagnesium bromide furnished alcohol 10. Functional group manipulation afforded (R)-2 in 49% overall yield from 5. DCC coupling of (R)-2 with 3-O-benzyl-1-O-palmitoyl-sn-glycerol (16), followed by hydrogenolytic removal of the benzyl group and treatment with benzyl bis(diisopropyl)phosphoramidite, afforded phosphoramidite 20. Tetrazole-mediated coupling of 20 with PIM1 head group 21 gave 22, and subsequent debenzylation afforded phosphatidylinositol mono-mannoside, PIM1 (23). Similarly, coupling of 20 and 24 and removal of the benzyl protecting groups gave PIM2 (1c). Both 23 and 1c have a clearly defined acylation pattern, which was confirmed by mass spectrometry, with sn-1 palmitoyl and sn-2 tuberculostearoyl groups on the glycerol moiety. Both 23 and 1c were shown to modulate the release of the pro-inflammatory cytokine, IL-12, in a dendritic cell assay.

  DOI：

  10.1021/jo0625599

文献信息

• Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis
  作者：Bjorn ter Horst、Chetan Seshadri、Lindsay Sweet、David C. Young、Ben L. Feringa、D. Branch Moody、Adriaan J. Minnaard

  DOI：10.1194/jlr.m001982

  日期：2010.5

  A glycerophospholipid (1-O-tuberculostearoyl-2-O -palmitoyl-sn-glycero-3-phosphoethanolamine) from Mycobacterium tuberculosis was isolated from the reference strain H37Rv. The molecular structure of this tuberculostearoyl [(R)-10-methyloctadecyl] and palmitoyl containing phosphatidylethanolamine (PE) has been resolved. The substitution pattern on the glycerol backbone could be determined by comparison of the isolate to the two synthetically prepared regioisomers. MS/MS analysis was used to determine its molecular structure. Production of this synthetic version of mycobacterial PE in high yield, with a stereochemically correct and pathogen-specific fatty acyl group, can be used as a standard in LC-MS based lipidomic analyses to detect trace amounts of mycobacterial PE in human blood, sputum, or tissues as a marker of infection by mycobacteria.-ter Horst, B., C. Seshadri, L. Sweet, D. C. Young, B. L. Feringa, D. B. Moody, and A. J. Minnaard. Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis. J. Lipid Res. 2010. 51: 1017-1022.