Polystyrene AM PAM Leu Acetyl Mercapto Trt

€ 91,00*

SIZE

100 - 200 mesh

Capacity

0.5 - 0.9 mmol/g

AMOUNT

Product number
H10090.1G

Product information

This resin can be used for the synthesis of peptide thioesters by Boc chemistry. After removal of the trityl protecting group by TFA/DCM treatment the first Boc amino acid is loaded to the resin by DIC/HOBt activation. Peptide synthesis follows the standard Boc synthesis protocol.
After finishing the peptide synthesis, the peptide thioester resin is treated by HF resulting in the deprotected peptide thioester derivative which can be used for native chemical ligation.

Literature

L 55 Thioester Resins for Chemical Ligation (Dawson Resins)

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.

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.

Review T. W. Muir et al., Methods in Enzymology (Ed. G. Fields) Academic Press, 266 ff.

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.

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.

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.

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.

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.

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.

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.

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