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Cleavage and deprotection of synthetic peptides by hydrolysis in subcritical water
KTH, School of Biotechnology (BIO).
2013 (English)Independent thesis Advanced level (degree of Master (Two Years)), 20 credits / 30 HE creditsStudent thesisAlternative title
Klyvning och avskyddning av syntetiska peptider genom hydrolys i subkritiskt vatten (Swedish)
Abstract [en]

Solid-Phase Peptide Sythesis (SPPS) is the method of choice for efficient peptide synthesis. SPPS is a stepwise method where a growing peptide is synthesised onto a linker molecule attached to a solid suuport (resin). In the final step of the synthesis, the peptide must be cleaved off from the lnker molcule and the protective groups removed concomitantly. This procedure is conventionally carried out with trifluoracetic acid (TFA). This is a corrosive and toxic chemical that is difficult to handle and requires special safety procedures for its disposal. Hence, it is of large interest to find a safer and a more environmentally friendly alternative. Therefore, the purpose of this study was to investigate if subcritical water under mild acidic conditions were achieved with the Biotage®  Initiator+ Microwave Synthesizer, limited to a maximum pressure of 30 bar. A temerature range of 200-230°C and pressures of 15.5-27.8 bar (where the dielectric constant of water is close to MeOH or DMF) was examined for various reaction times and pH, by addition of HCI, to find suitable conditions for efficient cleavage of amino acid-resin conjugates. The main part of the experiments was carried out on pre-loaded Fmoc-Ohe-Wang resin, where a maximum cleavage of 77% was obtained. Further studies should focus on the influence of subcritical conditions on amide bonds and side reactions that might occur. It should also be investigated if the conditions where cleavage of the Wang linker is obtained are sufficient for concomitant deprotection of the side chain protective groups, as is the case in conventional cleavage and deprotection.

Place, publisher, year, edition, pages
Keyword [en]
Subcritical water, peptide, Wang resin, solid phase peptide synthesis, SPPS, Fmox synthesis, microwave-assisted synthesis, microwave irradiation
National Category
Engineering and Technology
URN: urn:nbn:se:kth:diva-150563OAI: diva2:744725
Available from: 2015-04-17 Created: 2014-09-05 Last updated: 2015-09-18Bibliographically approved

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