Polystyrene Dawson MeDbz RAM Resin

Product information

This resin contains the Dawson MeDbz Rink Amide linker attached to aminomethylated polystyrene. It is a new type of support for the synthesis of C-terminal peptide aryl thioesters by Fmoc SPPS. When peptide assembly is finished in a follow up reaction a cyclic N-acylurea is formed which can either be converted to the desired aryl thioester by aryl thiol or directly used in native chemical ligation without prior isolation of the intermediate precursor.


L 55 Thioester Resins for Chemical Ligation (Dawson Resins)

  1. Dawson, P. E.; Kent, S. B. Synthesis of Native Proteins by Chemical Ligation. Annu. Rev. Biochem. 2000, 69 (1), 923-960. doi: 10.1146/annurev.biochem.69.1.923.
  2. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. Synthesis of Proteins by Native Chemical Ligation. Science 1994, 266 (5186), 776-779. doi: 10.1126/science.7973629.
  3. Review T. W. Muir et al., Methods in Enzymology (Ed. G. Fields) Academic Press, 266 ff.
  4. Dawson, P. E.; Churchill, M. J.; Ghadiri, M. R.; Kent, S. B. H. Modulation of Reactivity in Native Chemical Ligation through the Use of Thiol Additives. J. Am. Chem. Soc. 1997, 119 (19), 4325-4329. doi: 10.1021/ja962656r.
  5. Kent, S.B.H.; et al. Total Chemical Synthesis of Proteins: Evolution of Solid Phase Synthetic Methods Illustrated by Total Chemical Synthesis of the HIV-1 Protease, in Innovations and Perspectives in Solid Phase Synthesis, (Ed. R. Epton) Collected Papers of the Second International Symposium, 1991, Intercept Ltd., Andover, 1992, 1 22.
  6. Blanco-Canosa, J. B.; Dawson, P. E. An Efficient Fmoc-SPPS Approach for the Generation of Thioester Peptide Precursors for Use in Native Chemical Ligation. Angew. Chem. Int. Ed Engl. 2008, 47 (36), 6851-6855. doi: 10.1002/anie.200705471.
  7. Pentelute, B. L.; Barker, A. P.; Janowiak, B. E.; Kent, S. B. H.; Collier, R. J. A Semisynthesis Platform for Investigating Structure-Function Relationships in the N-Terminal Domain of the Anthrax Lethal Factor. ACS Chem. Biol. 2010, 5 (4), 359-364. doi: 10.1021/cb100003r.
  8. Mahto, S. K.; Howard, C. J.; Shimko, J. C.; Ottesen, J. J. A Reversible Protection Strategy to Improve Fmoc-SPPS of Peptide Thioesters by the N-Acylurea Approach. Chembiochem 2011, 12 (16), 2488-2494. doi: 10.1002/cbic.201100472.
  9. Gunasekera, S.; Aboye, T. L.; Madian, W. A.; El-Seedi, H. R.; Göransson, U. Making Ends Meet: Microwave-Accelerated Synthesis of Cyclic and Disulfide Rich Proteins via in Situ Thioesterification and Native Chemical Ligation. Int. J. Pept. Res. Ther. 2013, 19 (1), 43-54. doi: 10.1007/s10989-012-9331-y.
  10. Blanco-Canosa, J. B.; Nardone, B.; Albericio, F.; Dawson, P. E. Chemical protein synthesis using a second-generation N-acylurea linker for the preparation of peptide-thioester precursors. Journal of the American Chemical Society, 2015, 137(22), 7197-7209. doi: 10.1021/jacs.5b03504.
  11. Cistrone, P. A., Bird, M. J., Flood, D. T., Silvestri, A. P., Hintzen, J. C. J., Thompson, D. A., Dawson, P. E. Native Chemical Ligation of Peptides and Proteins. Curr. Protoc. Chem. Biol. 2019;11 (1):e61. doi: 10.1002/cpch.61