[1-[[[(2R)-2-羧基-2-[[(9H-芴-9-基甲氧基)羰基]氨基]乙基]硫基]甲基]-1,2-乙二基]双十六烷酸酯 | 210532-98-2

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: [1-[[[(2R)-2-羧基-2-[[(9H-芴-9-基甲氧基)羰基]氨基]乙基]硫基]甲基]-1,2-乙二基]双十六烷酸酯
• 英文名称: N-fluorenylmethoxycarbonyl-S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-(R)-cysteine
• 英文别名: Fmoc-Cys((RS)-2,3-di(palimitoyloxy)propyl)-OH；Fmoc-Cys((RS)-2,3-di(palmitoyloxy)propyl)OH；Fmoc-Cys((RS)-2,3-di(palmitoyloxy)-propyl)-OH；(2R)-3-[2,3-di(hexadecanoyloxy)propylsulfanyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 210532-98-2
• 化学式: C₅₃H₈₃NO₈S
• 分子量: 894.31
• InChiKey: HNJKCVLFJLXANK-IYXDIJEESA-N

物化性质

• 沸点：
  922.7±65.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  17.8
• 重原子数：
  63
• 可旋转键数：
  42
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [1-[[[(2R)-2-羧基-2-[[(9H-芴-9-基甲氧基)羰基]氨基]乙基]硫基]甲基]-1,2-乙二基]双十六烷酸酯 、 棕榈酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 以78%的产率得到N-palmitoyl-S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-(R)-cysteinyl-(S)-serine
  参考文献：
  名称：

  Stereochemical Dependence of the Self-Assembly of the Immunoadjuvants Pam₃Cys and Pam₃Cys-Ser

  摘要：

  The lipopeptide tripalmitoyl-S-glycerylcysteine (Pam(3)Cys) is derived from the N-terminal part of bacterial lipopeptides and is a polyclonal B-lymphocyte and macrophage activator. Derivatives of Pam(3)Cys constitute highly potent, nontoxic immunoadjuvants, and lipopeptide-antigen conjugates have found important applications as novel fully synthetic low-molecular-weight vaccines. To establish a possible correlation between molecular structure, aggregation properties, and biological activities, we have studied the self-assembly and monolayer properties of a range of Pam(3)Cys derivatives using transmission electron microscopy (TEM) and a Langmuir-film balance combined with a Brewster angle microscopy (BAM). It was found that the chirality of the glyceryl moiety and the additional serine unit impacted on the mode of aggregation and the monolayer properties. Correlations are discussed between these physicochemical properties and biological activities.

  DOI：

  10.1021/ja991319q
• 作为产物：
  描述：

  Fmoc-S-三苯甲基-L-半胱氨酸 在 4-二甲氨基吡啶 、 三异丙基硅烷 、 palladium on activated charcoal 、 氢气 、 四丁基碘化铵 、 caesium carbonate 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.5h， 生成 [1-[[[(2R)-2-羧基-2-[[(9H-芴-9-基甲氧基)羰基]氨基]乙基]硫基]甲基]-1,2-乙二基]双十六烷酸酯
  参考文献：
  名称：

  Fully synthetic self-adjuvanting MUC1-fibroblast stimulating lipopeptide 1 conjugates as potential cancer vaccines

  摘要：

  我们已经设计并合成了MUC1-纤维母细胞刺激脂肽1共轭物，作为潜在的自身佐剂癌症疫苗，采用线性固相肽合成策略。

  DOI：

  10.1039/c6cc04623a

文献信息

• IMMUNOGENIC VACCINE
  申请人：University of Georgia Research Foundation, Inc.

  公开号：US20150299290A1

  公开（公告）日：2015-10-22

  A glycolipopeptide comprising a carbohydrate component, a lipid component, and a MUC1 peptide component that induces both a humoral and a cellular immune response for use as a therapeutic or prophylactic vaccine.

  一种含有碳水化合物组分、脂质组分和MUC1肽组分的糖脂肽，可诱导细胞免疫和体液免疫反应，用作治疗或预防性疫苗。
• Molecular Imaging of Cancer Cells In Vivo
  申请人：Morse David L.

  公开号：US20140161725A1

  公开（公告）日：2014-06-12

  Cellular targets on cancer cells have been identified that can be used with targeted molecular imaging to detect the cancer cells in vivo. Non-invasive methods for detecting cancer cells, such as metastasized cancer cells, are therefore provided. Also provided are compositions and kits for use in the disclosed methods.

  已经确定了可用于与靶向分子成像结合以在体内检测癌细胞的癌细胞细胞靶点。因此提供了用于检测癌细胞的非侵入性方法，例如转移性癌细胞。还提供了用于所述方法的组合物和试剂盒。
• Molecular imaging of cancer cells in vivo
  申请人：Morse David L.

  公开号：US10406248B2

  公开（公告）日：2019-09-10

  Cellular targets on cancer cells have been identified that can be used with targeted molecular imaging to detect the cancer cells in vivo. Non-invasive methods for detecting cancer cells, such as metastasized cancer cells, are therefore provided. Also provided are compositions and kits for use in the disclosed methods.

  癌细胞上的细胞靶点已被确定，可与靶向分子成像一起用于检测体内的癌细胞。因此，本文提供了检测癌细胞（如转移癌细胞）的非侵入性方法。此外，还提供了用于所公开方法的组合物和试剂盒。
• [EN] MOLECULAR IMAGING OF CANCER CELLS IN VIVO<br/>[FR] IMAGERIE MOLÉCULAIRE DE CELLULES CANCÉREUSES IN VIVO
  申请人：H LEE MOFFITT CANCER CT & RES

  公开号：WO2013036543A3

  公开（公告）日：2013-05-02
• Glycolipopeptide and uses thereof
  申请人：Boons Geert-Jan

  公开号：US20090041836A1

  公开（公告）日：2009-02-12

  A glycolipopeptide comprising a carbohydrate component, a peptide component and a lipid component, for use as a therapeutic or prophylactic vaccine. Also provided are monoclonal and polyclonal antibodies that recognize the glycolipopeptide of the invention, as well as uses thereof.