Microwave-assisted TFA cleavage of peptides from Merrifield resin
Article first published online: 10 NOV 2009
Copyright © 2009 European Peptide Society and John Wiley & Sons, Ltd.
Journal of Peptide Science
Volume 16, Issue 1, pages 31–39, January 2010
How to Cite
Kluczyk, A., Rudowska, M., Stefanowicz, P. and Szewczuk, Z. (2010), Microwave-assisted TFA cleavage of peptides from Merrifield resin. J. Peptide Sci., 16: 31–39. doi: 10.1002/psc.1191
- Issue published online: 4 DEC 2009
- Article first published online: 10 NOV 2009
- Manuscript Accepted: 7 SEP 2009
- Manuscript Revised: 28 AUG 2009
- Manuscript Received: 13 JUL 2009
- microwave-assisted synthesis;
- Merrifield resin;
- protecting groups
Microwave-assisted (MW) reactions are of special interest to the chemical community due to faster reaction times, cleaner reactions and higher product yields. The adaptation of MW to solid phase peptide synthesis resulted in spectacular syntheses of difficult peptides. In the case of Merrifield support, used frequently in synthesis of special peptides, the conditions used in product cleavage are not compatible with off-resin monitoring of the reaction progress. The application of MW irradiation in product removal from Merrifield resin using trifluoroacetic acid (TFA) was investigated using model tetrapeptides and the effects were compared with standard trifluoromethanesulphonic acid (TFMSA) cleavage using elemental analysis as well as chromatographic (HPLC) and spectroscopic (IR) methods. The deprotection of benzyloxycarbonyl and benzyl groups in synthetic bioactive peptides was analyzed using LC-MS and MS/MS experiments. In a 5 min microwave-assisted TFA reaction at low temperature, the majority of product is released from the resin, making the analytical scale MW-assisted procedure a method of choice in monitoring the reactions carried out on Merrifield resin due to the short reaction time and compatibility with HPLC and ESI-MS conditions. Copyright © 2009 European Peptide Society and John Wiley & Sons, Ltd.