Solid-phase peptide synthesis by fragment condensation: Coupling in swelling volume |
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Authors: | Markéta Rinnová Milan Souek and Michal Lebl |
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Institution: | (1) Institute of Organic Chemistry and Biochemistry, Flemingovo n. 2, Prague 6, CZ-166 10, Czech Republic;(2) Trega Biosciences Inc., 3550 General Atomics Court, San Diego, CA, 92121, U.S.A |
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Abstract: | The condensation of short peptides to resin-bound fragments was examined with respect to high coupling yields with only a small molar excess of a peptide in the reaction solution. The best results were achieved by the addition of reactants (C-unprotected peptide, DIC, and HOBt) dissolved in a so-called swelling volume of an appropriate solvent to a dry resin with an attached N-deprotected peptide chain. Each coupling step was followed by the end-capping of unreacted resin-bound peptide with 2,4-dinitrofluorobenzene. The substituted dinitroaniline chromophore formed in this reaction made the detection and separation of deletion peptides easy. Both conventional and swelling volume methods were compared on parallel syntheses of the HIV-1 protease C-terminal 78–99 fragment. The yields of the isolated heneicosapeptide were 21 and 81% in favor of the swelling volume procedure. |
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Keywords: | convergent peptide synthesis end-capping with 2 4-dinitrofluorobenzene protected peptide |
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