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Convenient synthesis of thioamidated peptides and proteins

Khatri, B and Bhat, P and Chatterjee, J (2020) Convenient synthesis of thioamidated peptides and proteins. In: Journal of Peptide Science, 26 (4-5).

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Official URL: https://dx.doi.org/10.1002/psc.3248


The unique physicochemical properties of a thioamide bond, which is an ideal isostere of an amide bond, have not been fully exploited because of the tedious synthesis of thionated amino acid building blocks. Here, we report a purification-free and highly efficient synthesis of thiobenzotriazolides of Fmoc-protected and orthogonally protected 20 naturally occurring amino acids including asparagine, glutamine, and histidine. The near-quantitative conversion to the respective thioamidated peptides on solid support demonstrates the robustness of the synthetic route. Furthermore, the unaltered incorporation efficiency of thiobenzotriazolides from their stock solution till 48 h suggests their compatibility toward automated peptide synthesis. Finally, utilizing an optimized cocktail of 2 DBU + 5 piperazine for fast Fmoc-deprotection, we report the synthesis of a thioamidated Pin1 WW domain and thioamidated GB1 directly on solid support.

Item Type: Journal Article
Publication: Journal of Peptide Science
Publisher: John Wiley and Sons Ltd
Additional Information: The copyright of this article belongs to John Wiley and Sons Ltd
Department/Centre: Division of Biological Sciences > Molecular Biophysics Unit
Date Deposited: 18 Jun 2020 10:14
Last Modified: 18 Jun 2020 10:14
URI: http://eprints.iisc.ac.in/id/eprint/65076

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