(2S)-2-[[(2S)-6-[[4-[(1S,2R)-1-benzamido-3-[[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl]oxy]-3-oxo-1-phenylpropan-2-yl]oxy-4-oxobutanoyl]amino]-2-[[(2S)-2-[[(2S)-2-[(2-naphthalen-2-ylacetyl)amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]hexanoyl]amino]-3-(4-phosphonooxyphenyl)propanoic acid | 1187460-17-8

• 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: (2S)-2-[[(2S)-6-[[4-[(1S,2R)-1-benzamido-3-[[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl]oxy]-3-oxo-1-phenylpropan-2-yl]oxy-4-oxobutanoyl]amino]-2-[[(2S)-2-[[(2S)-2-[(2-naphthalen-2-ylacetyl)amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]hexanoyl]amino]-3-(4-phosphonooxyphenyl)propanoic acid
• CAS: 1187460-17-8
• 化学式: C₉₆H₁₀₃N₆O₂₆P
• 分子量: 1787.87
• InChiKey: GDZGDRIBUBIWIU-GECIYKNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  129
• 可旋转键数：
  42
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  477
• 氢给体数：
  11
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  (2S)-2-[[(2S)-6-[[4-[(1S,2R)-1-benzamido-3-[[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl]oxy]-3-oxo-1-phenylpropan-2-yl]oxy-4-oxobutanoyl]amino]-2-[[(2S)-2-[[(2S)-2-[(2-naphthalen-2-ylacetyl)amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]hexanoyl]amino]-3-(4-phosphonooxyphenyl)propanoic acid 在 alkaline phosphatase 作用下， 以 水 为溶剂， 生成 (2S)-2-[[(2S)-6-[[4-[(1S,2R)-1-benzamido-3-[[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl]oxy]-3-oxo-1-phenylpropan-2-yl]oxy-4-oxobutanoyl]amino]-2-[[(2S)-2-[[(2S)-2-[(2-naphthalen-2-ylacetyl)amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoic acid
  参考文献：
  名称：

  Enzyme-Instructed Molecular Self-assembly Confers Nanofibers and a Supramolecular Hydrogel of Taxol Derivative

  摘要：

  By covalently connecting taxol with a motif that is prone to self-assemble, we successfully generate the precursor (5a), the hydrogelator (5b), and hydrogel of a taxol derivative without compromising the cytotoxic activity of the taxol. This approach promises a general method to create nanofibers of therapeutic molecules that have a dual role, as both the delivery vehicle and the drug, itself.

  DOI：

  10.1021/ja904411z
• 作为产物：
  描述：

  2-(naphthalen-2-yl)acetyl-(L)-Phe-(L)-Phe-(L)-Lys-(L)-Tyr phosphate 、 2'-NHS-succinylpaclitaxel 在 sodium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 生成 (2S)-2-[[(2S)-6-[[4-[(1S,2R)-1-benzamido-3-[[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl]oxy]-3-oxo-1-phenylpropan-2-yl]oxy-4-oxobutanoyl]amino]-2-[[(2S)-2-[[(2S)-2-[(2-naphthalen-2-ylacetyl)amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]hexanoyl]amino]-3-(4-phosphonooxyphenyl)propanoic acid
  参考文献：
  名称：

  [EN] ANTINEOPLASTIC HYDROGELS, AND ENZYME-INSTRUCTED PREPARATIONS THEREOF
  [FR] HYDROGELS ANTINÉOPLASIQUES ET PRÉPARATIONS À MÉDIATION ENZYMATIQUE DE CEUX-CI

  摘要：

  公开号：

  WO2010151644A3

文献信息

• Targeting a Homogeneously Glycosylated Antibody Fc To Bind Cancer Cells Using a Synthetic Receptor Ligand
  作者：Junpeng Xiao、Rui Chen、Mark A. Pawlicki、Thomas J. Tolbert

  DOI：10.1021/ja9045179

  日期：2009.9.30

  The targeting of a glycosylated antibody Fc fragment to bind to cancer cells by site-selective incorporation of a synthetic ligand is described. Homogeneously glycosylated immunoglobulin G subclass 1 fragment crystallizable (IgG1 Fc) was produced by expression in a glycosylation-deficient yeast strain and subsequent treatment with mannosidase IA. A N-terminal cysteine was generated on the expressed IgG1 Fc by utilizing proteolytic processing enzymes in the yeast secretory pathway. A cyclic RGD peptide thioester 2 was synthesized and then site-selectively attached to the N-terminus of the IgG1 Fc glycoprotein using native chemical ligation. The resulting chemically modified antibody fragment, RGD-Man(5)-IgG1 Fc (5), retained biological activity similar to that of the free cyclic RGD peptide 1 when assayed for its ability to both promote and inhibit the adhesion of alpha(v)beta(3) integrin receptor-ex pressing WM-115 melanoma cells. In addition, fluorescent microscopy experiments were conducted using FITC-labeled 5 and confirmed binding of 5 to WM-115 melanoma cells. Site-selectively modified antibody fragments such as the one described here may be used to combine the beneficial properties of synthetic receptor ligands with antibody fragments to develop useful biochemical tools and improved therapeutics. The methods described here can also be used to produce glycoprotein fragments for the chemoenzymatic synthesis of homogeneous glycoproteins.