Solid-phase synthesis of c(RGDfK) derivatives: on-resin cyclisation and lysine functionalisation
作者： Catherine F McCusker , Philip J Kocienski , F.Thomas Boyle , Andreas G Schätzlein
DOI: 10.1016/S0960-894X(01)00799-5
关键词:
摘要: The cyclic pentapeptide c(RGDfK), a selective ligand for the alpha(v)beta3 integrin, was synthesised on solid phase. All synthetic operations including cyclisation step and appendage of Bolton-Hunter reagent conducted on-resin.
elsevier.com
sci-hub.se 参考文章(26)
Louis A. Carpino, Hitesh Shroff, Salvatore A. Triolo, El-Sayed M.E. Mansour, Holger Wenschuh, Fernando Albericio, The 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl group (Pbf) as arginine side chain protectant Tetrahedron Letters. ,vol. 34, pp. 7829- 7832 ,(1993) , 10.1016/S0040-4039(00)61487-9
Edward F. Plow, Thomas A. Haas, Li Zhang, Joseph Loftus, Jeffrey W. Smith, Ligand Binding to Integrins Journal of Biological Chemistry. ,vol. 275, pp. 21785- 21788 ,(2000) , 10.1074/JBC.R000003200
William J. Pitts, John Wityak, Joanne M. Smallheer, A. Ewa Tobin, James W. Jetter, Jennifer S. Buynitsky, Patricia P. Harlow, Kimberly A. Solomon, Martha H. Corjay, Shaker A. Mousa, Ruth R. Wexler, Prabhakar K. Jadhav, Isoxazolines as Potent Antagonists of the Integrin αvβ3 Journal of Medicinal Chemistry. ,vol. 43, pp. 27- 40 ,(2000) , 10.1021/JM9900321
Alvin C. Bach, J. Robert Espina, Sharon A. Jackson, Pieter F. W. Stouten, Jodie L. Duke, Shaker A. Mousa, William F. DeGrado, Type II‘ to Type I β-Turn Swap Changes Specificity for Integrins Journal of the American Chemical Society. ,vol. 118, pp. 293- 294 ,(1996) , 10.1021/JA953163+
K.C. Nicolaou, John I. Trujillo, Bernd Jandeleit, Kelly Chibale, M. Rosenfeld, B. Diefenbach, D.A. Cheresh, S.L. Goodman, Design, synthesis and biological evaluation of nonpeptide integrin antagonists. Bioorganic & Medicinal Chemistry. ,vol. 6, pp. 1185- 1208 ,(1998) , 10.1016/S0968-0896(98)00090-X
Roland Haubner, Dirk Finsinger, Horst Kessler, Stereoisomeric Peptide Libraries and Peptidomimetics for Designing Selective Inhibitors of the αvβ3 Integrin for a New Cancer Therapy Angewandte Chemie. ,vol. 36, pp. 1374- 1389 ,(1997) , 10.1002/ANIE.199713741
Elisabeth Lohof, Eckart Planker, Christian Mang, Fred Burkhart, Michael A. Dechantsreiter, Roland Haubner, Hans-Jürgen Wester, Markus Schwaiger, Günther Hölzemann, Simon L. Goodman, Horst Kessler, Carbohydrate Derivatives for Use in Drug Design: Cyclicαv-Selective RGD Peptides Angewandte Chemie. ,vol. 39, pp. 2761- 2764 ,(2000) , 10.1002/1521-3773(20000804)39:15<2761::AID-ANIE2761>3.0.CO;2-9
J. Wermuth, S. L. Goodman, A. Jonczyk, H. Kessler, Stereoisomerism and Biological Activity of the Selective and Superactive αvβ3 Integrin Inhibitor cyclo(-RGDfV-) and Its Retro-Inverso Peptide Journal of the American Chemical Society. ,vol. 119, pp. 1328- 1335 ,(1997) , 10.1021/JA961908L
Roland Haubner, Rainer Gratias, Beate Diefenbach, Simon L. Goodman, Alfred Jonczyk, Horst Kessler, Structural and Functional Aspects of RGD-Containing Cyclic Pentapeptides as Highly Potent and Selective Integrin αVβ3 Antagonists Journal of the American Chemical Society. ,vol. 118, pp. 7461- 7472 ,(1996) , 10.1021/JA9603721
Anusch Peyman, Volkmar Wehner, Jochen Knolle, Hans Ulrich Stilz, Gerhard Breipohl, Karl-Heinz Scheunemann, Denis Carniato, Jean-Marie Ruxer, Jean-Francois Gourvest, Thomas R Gadek, Sarah Bodary, RGD Mimetics containing a central hydantoin scaffold: αVβ3 vs αIIbβ3 selectivity requirements Bioorganic & Medicinal Chemistry Letters. ,vol. 10, pp. 179- 182 ,(2000) , 10.1016/S0960-894X(99)00661-7