N-fluorenylmethoxycarbonyl-S-[2,3-dihydroxy-(2RS)-propyl]-(R)-cysteine tert-butyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-fluorenylmethoxycarbonyl-S-[2,3-dihydroxy-(2RS)-propyl]-(R)-cysteine tert-butyl ester
• 英文别名: tert-butyl (2R)-3-(2,3-dihydroxypropylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• 化学式: C₂₅H₃₁NO₆S
• 分子量: 473.59
• InChiKey: MTFAGSRDAYEFPW-XLDIYJRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-fluorenylmethoxycarbonyl-S-[2,3-dihydroxy-(2RS)-propyl]-(R)-cysteine tert-butyl ester 在 4-二甲氨基吡啶 、 碳酸二异丙酯 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 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：

  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：

  缩水甘油 、 二(2-甲基-2-丙基) N,N'-二[(9H-芴-9-基甲氧基)羰基]-L-半胱氨酰锡酸酯 在 盐酸 、 硫酸 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 以84%的产率得到N-fluorenylmethoxycarbonyl-S-[2,3-dihydroxy-(2RS)-propyl]-(R)-cysteine tert-butyl ester
  参考文献：
  名称：

  使用 FRET 报告基因探测细菌脂蛋白信号肽酶的底物识别

  摘要：

  脂蛋白信号肽酶 (Lsp) 是一种跨膜天冬氨酸蛋白酶，在细菌脂蛋白成熟途径中起关键作用。尽管 Lsp 在细菌界普遍使用，并且具有作为抗生素靶点的潜力，但对 Lsp 的底物识别模式知之甚少。在这里，我们使用基于合成肽的 FRET 报告基因研究了来自革兰氏 -（大肠杆菌）和革兰氏 +（化脓性链球菌）细菌的 Lsp 的底物识别和生化特性。发现双癸酰甘油是最佳脂质长度，并且 Lsp 显示出对 (R) 形式的二酰基甘油具有独特的对映选择性。我们的研究将促进体外 Lsp 检测的迭代优化，并提供对 Lsp 底物范围的第一次化学询问。

  DOI：

  10.1002/1873-3468.13155

文献信息

• 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
• Stereochemical Dependence of the Self-Assembly of the Immunoadjuvants Pam₃Cys and Pam₃Cys-Ser
  作者：Frank Reichel、Annie M. Roelofsen、Hubertus P. M. Geurts、Taina I. Hämäläinen、Martinus C. Feiters、Geert-Jan Boons

  DOI：10.1021/ja991319q

  日期：1999.9.1

  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.
• Probing substrate recognition of bacterial lipoprotein signal peptidase using FRET reporters
  作者：Seiya Kitamura、Dennis W. Wolan

  DOI：10.1002/1873-3468.13155

  日期：2018.7

  maturation pathway. Despite the universal use of Lsp across the Bacterial Kingdom and its potential as an antibiotic target, the substrate recognition patterns of Lsp are poorly understood. Here, we investigated the substrate recognition and biochemical properties of Lsp from Gram− (Escherichia coli) and Gram+ (Streptococcus pyogenes) bacteria, using synthetic peptide‐based FRET reporters. Didecanoyl glycerol

  脂蛋白信号肽酶 (Lsp) 是一种跨膜天冬氨酸蛋白酶，在细菌脂蛋白成熟途径中起关键作用。尽管 Lsp 在细菌界普遍使用，并且具有作为抗生素靶点的潜力，但对 Lsp 的底物识别模式知之甚少。在这里，我们使用基于合成肽的 FRET 报告基因研究了来自革兰氏 -（大肠杆菌）和革兰氏 +（化脓性链球菌）细菌的 Lsp 的底物识别和生化特性。发现双癸酰甘油是最佳脂质长度，并且 Lsp 显示出对 (R) 形式的二酰基甘油具有独特的对映选择性。我们的研究将促进体外 Lsp 检测的迭代优化，并提供对 Lsp 底物范围的第一次化学询问。