N-[(R)-3-decanoyloxytetradecanoyl]-D-serine benzyl ester | 216014-07-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(R)-3-decanoyloxytetradecanoyl]-D-serine benzyl ester
• 英文别名: [(3R)-1-[[(2R)-3-hydroxy-1-oxo-1-phenylmethoxypropan-2-yl]amino]-1-oxotetradecan-3-yl] decanoate
• CAS: 216014-07-2
• 化学式: C₃₄H₅₇NO₆
• 分子量: 575.83
• InChiKey: YSFUFJVYYMALDA-FIRIVFDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  41
• 可旋转键数：
  28
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(R)-3-decanoyloxytetradecanoyl]-D-serine benzyl ester 在 吡啶 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 、 4-吡咯烷基吡啶 、 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide methiodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Characterization of TRIF selectivity in the AGP class of lipid A mimetics: Role of secondary lipid chains

  摘要：

  TLR4 agonists that favor TRIF-dependent signaling and the induction of type 1 interferons may have potential as vaccine adjuvants with reduced toxicity. CRX-547 (4), a member of the aminoalkyl glucosaminide 4-phosphate (AGP) class of lipid A mimetics possessing three (R)-3-decanoyloxytetradecanoyl groups and D-relative configuration in the aglycon, selectively reduces MyD88-dependent signaling resulting in TRIF-selective signaling, whereas the corresponding secondary ether lipid 6a containing (R)-3-decyloxytetradecanoyl groups does not. In order to determine which secondary acyl groups are important for the reduction in MyD88-dependent signaling activity of 4, the six possible ester/ether hybrid derivatives of 4 and 6a were synthesized and evaluated for their ability to induce NF-kappa B in a HEK293 cell reporter assay. An (R)-3-decanoyloxytetradecanoyl group on the 3-position of the D-glucosamine unit was found to be indispensable for maintaining low NF-kappa B activity irrespective of the substitutions (decyl or decanoyl) on the other two secondary positions. These results suggest that the carbonyl group of the 3-secondary lipid chain may impede homodimerization and/or conformational changes in the TLR4-MD2 complex necessary for MyD88 binding and pro-inflammatory cytokine induction. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.024
• 作为产物：
  描述：

  (R)-3-decanoyloxytetradecanoic acid 在 EDC.MeI 作用下， 以 二氯甲烷 为溶剂， 以1.05 g (91%)的产率得到N-[(R)-3-decanoyloxytetradecanoyl]-D-serine benzyl ester
  参考文献：
  名称：

  Aminoalkyl glucosaminide phosphate compounds and their use as adjuvants and immunoeffectors

  摘要：

  描述和声明了一种作为辅助剂和免疫效应物的氨基糖脂磷酸酯（AGP）化合物。这些化合物具有一个2-脱氧-2-氨基葡萄糖与一个氨基烷基（糖苷）基团的糖苷键连接。这些化合物在葡萄糖氨基环上的4或6碳上磷酸化，并包括三个3-烷酰氧烷酰基。这些化合物增强了免疫动物中的抗体产生，同时刺激细胞因子的产生并激活巨噬细胞。还公开了将这些化合物用作辅助剂和免疫效应物的组合物和方法。

  公开号：

  US20030092643A1

文献信息

• Aminoalkyl glucosamine phosphate compounds and their use as adjuvants and immunoeffectors
  申请人：Corixa Corporation

  公开号：US06355257B1

  公开（公告）日：2002-03-12

  Aminoalkyl glucosamine phosphate compounds that are adjuvants and immunoeffectors are described and claimed. The compounds have a 2-deoxy-2-amino glucose in glycosidic linkage with an aminoalkyl (aglycon) group. Compounds are phosphorylated at the 4 or 6 carbon on the glucosamine ring and comprise three 3-alkanoyloxyalkanoyl residues. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Methods for using the compounds as adjuvants and immunoeffectors are also disclosed.

  描述和声明了一种氨基糖胺磷酸盐化合物，它们是辅助剂和免疫效应物质。这些化合物具有一个2-脱氧-2-氨基葡萄糖与一个氨基烷基（非糖部分）基团的糖苷键连接。这些化合物在葡萄糖胺环上的4或6碳上磷酸化，并包括三个3-烷酰氧烷酰残基。这些化合物增强了免疫动物中的抗体产生，同时刺激细胞因子的产生并激活巨噬细胞。还公开了将这些化合物用作辅助剂和免疫效应物质的方法。
• Synthesis and biological evaluation of a new class of vaccine adjuvants: aminoalkyl glucosaminide 4-phosphates (AGPs)
  作者：David A. Johnson、C. Gregory Sowell、Craig L. Johnson、Mark T. Livesay、David S. Keegan、Michael J. Rhodes、J. Terry Ulrich、Jon R. Ward、John L. Cantrell、Valerie G. Brookshire

  DOI：10.1016/s0960-894x(99)00374-1

  日期：1999.8

  A novel series of acylated omega-aminoalkyl 2-amino-2-deoxy-4-phosphono-beta-D-glucopyranosides (aminoalkyl glucosaminide 4-phosphates) was synthesized and screened for immunostimulant activity. Several of these compounds enhance the production of tetanus toroid-specific antibodies in mice and augment vaccine-induced cytotoxic T cells against EG.7-ova target cells. (C) 1999 Elsevier Science Ltd. Pill rights reserved.
• AMINOALKYL GLUCOSAMINE PHOSPHATE COMPOUNDS AND THEIR USE AS ADJUVANTS AND IMMUNOEFFECTORS
  申请人：CORIXA CORPORATION

  公开号：EP0983286B1

  公开（公告）日：2004-07-28
• AMINOALKYL GLUCOSAMINIDE PHOSPHATE COMPOUNDS AND THEIR USE AS ADJUVANTS AND IMMUNOEFFECTORS
  申请人：CORIXA CORPORATION

  公开号：EP1230250A2

  公开（公告）日：2002-08-14
• US6113918A
  申请人：——

  公开号：US6113918A

  公开（公告）日：2000-09-05