TentaGel® S Dawson MeDbz RAM Resin

Product information

TentaGel® resins are grafted copolymers consisting of a low crosslinked polystyrene matrix on which polyethylene glycol (PEG or POE) is grafted via an ethyl ether group which increases stability towards acid treatment and minimizes PEG-leaching. The graft copolymer shows modified physicochemical properties which are highly dominated by the PEG moiety (and no longer by the polystyrene matrix) and has hydrophobic and hydrophilic properties. These copolymers are pressure stable and can be used in batch processes as well as under continuous flow conditions. The PEG spacer is in the range of MW 3000 Da. TentaGel® resins have high diffusion rates and excellent swelling in a wide range of solvents from e.g. toluene to water.
This resin contains the Dawson MeDbz Rink Amide linker attached to amino TentaGel® resin. 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