Highly efficient and selective phosphorylation of amino acid derivatives and polyols catalysed by 2-aryl-4-(dimethylamino)pyridine-N-oxides – towards kinase-like reactivity

作者: James I. Murray , Rudiger Woscholski , Alan C. Spivey

DOI: 10.1039/C4CC05388E

关键词: Amino acidArylReactivity (chemistry)PyridineCatalysisKinaseStereochemistryTyrosinePhosphorylationChemistry

摘要: The chemoselective phosphorylation of hydroxyl containing amino acid derivatives and polyols by phosphoryl chlorides catalyzed by 2-aryl-4-(dimethylamino)pyridine-N-oxides is described.

参考文章(30)
Bianca R. Sculimbrene, Scott J. Miller, Discovery of a catalytic asymmetric phosphorylation through selection of a minimal kinase mimic: a concise total synthesis of D-myo-inositol-1-phosphate. Journal of the American Chemical Society. ,vol. 123, pp. 10125- 10126 ,(2001) , 10.1021/JA016779+
Joern Dengjel, Irina Kratchmarova, Blagoy Blagoev, Receptor tyrosine kinase signaling: a view from quantitative proteomics. Molecular BioSystems. ,vol. 5, pp. 1112- 1121 ,(2009) , 10.1039/B909534A
Bianca R. Sculimbrene, Adam J. Morgan, Scott J. Miller, Enantiodivergence in small-molecule catalysis of asymmetric phosphorylation: concise total syntheses of the enantiomeric D-myo-inositol-1-phosphate and D-myo-inositol-3-phosphate. Journal of the American Chemical Society. ,vol. 124, pp. 11653- 11656 ,(2002) , 10.1021/JA027402M
Ilse Manet, Sandra Monti, Pietro Bortolus, Maurizio Fagnoni, Angelo Albini, The photochemistry of 4-chlorophenol in water revisited: the effect of cyclodextrins on cation and carbene reactions. Chemistry: A European Journal. ,vol. 11, pp. 4274- 4282 ,(2005) , 10.1002/CHEM.200401227
Zhihong O'Brien, Mehran Fallah Moghaddam, Small molecule kinase inhibitors approved by the FDA from 2000 to 2011: a systematic review of preclinical ADME data Expert Opinion on Drug Metabolism & Toxicology. ,vol. 9, pp. 1597- 1612 ,(2013) , 10.1517/17425255.2013.834046
S. K. Grant, Therapeutic protein kinase inhibitors. Cellular and Molecular Life Sciences. ,vol. 66, pp. 1163- 1177 ,(2009) , 10.1007/S00018-008-8539-7
Yanling K. Wang, Wei Chen, Derek Blair, Mingming Pu, Yingju Xu, Scott J. Miller, Alfred G. Redfield, Thomas C. Chiles, Mary F. Roberts, Insights into the structural specificity of the cytotoxicity of 3-deoxyphosphatidylinositols. Journal of the American Chemical Society. ,vol. 130, pp. 7746- 7755 ,(2008) , 10.1021/JA710348R
Gerard Manning, David B Whyte, Ricardo Martinez, Tony Hunter, Sucha Sudarsanam, The Protein Kinase Complement of the Human Genome Science. ,vol. 298, pp. 1912- 1934 ,(2002) , 10.1126/SCIENCE.1075762
Yanling Karen Wang, Adam Morgan, Kimberly Stieglitz, Boguslaw Stec, Benjamin Thompson, Scott J. Miller, Mary F. Roberts, The temperature dependence of the inositol monophosphatase Km correlates with accumulation of di-myo-inositol 1,1'-phosphate in Archaeoglobus fulgidus. Biochemistry. ,vol. 45, pp. 3307- 3314 ,(2006) , 10.1021/BI052467Y
Yingju Xu, Bianca R. Sculimbrene, Scott J. Miller, Streamlined synthesis of phosphatidylinositol (PI), PI3P, PI3,5P2, and deoxygenated analogues as potential biological probes. Journal of Organic Chemistry. ,vol. 71, pp. 4919- 4928 ,(2006) , 10.1021/JO060702S