| Title | The use of electrochemical methods for deprotection during peptide synthesis | |
| Authors | Paula M.T. Ferreira, Hernani L.S. Maia, Luis S. Monteiro, Mario R.J. Rebelo and Ligia Rodrigues
Department of Chemistry, University of Minho, Gualtar, P-4700 BRAGA, Portugal |
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| Citation | Ferreira, P.M.T., Maia, H.L.S., Monteiro, L.S., Rebelo, M.R.J., Rodrigues, L.: The use of electrochemical methods for deprotection during peptide synthesis, Epitheorese Klin. Farmakol. Farmakokinet. 9(2-3): 83-87 (1995) | |
| Publication Date | 1995 | |
| Full Text Language | English | |
| Order – Buy | Ηλεκτρονική Μορφή: pdf (10 €) – Digital Type: pdf (10 €)
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| Keywords | Peptide synthesis, cathodic cleavage, amine protecting groups, electrochemistry. | |
| Other Terms | review article | |
| Summary | Throughout the last three decades several authors have investigated the behaviour of various protecting groups towards electrochemical reduction. However, most of this work was carried out on analytical scale and in many cases the experimental procedures were not recorded in sufficient detail to allow reproduction of the results described. In a few instances the authors obtained interesting results for preparative purposes, but met difficulties in the isolation of the reaction product. During the last decade we have been involved in the detailed investigation of the electrochemical behaviour of various protecting groups having in mind to explore the possibility of using this technique as a general procedure for deprotection in polyamine and peptide synthesis. Our early studies were focused on the investigation of the mechanisms of cleavage, which at a later stage enabled us to improve the experimental conditions with regard to reaction yields, to develop isolation procedures and to scale up to preparative reactions. This was mainly concerned with the appropriate choice of proton donors and supporting electrolytes in cathodic reactions. However, additional problems such as simultaneous reduction of other functional groups and racemization caused by strong bases generated during electrolysis had to be investigated. We have thus studied a selection of groups for amine protection suitable for cleavage at different potentials and also developed a strategy for selective protection and deprotection in polyamine synthesis. The amount of racemization occurring during cathodic cleavage of the benzyloxycarbonyl and tosyl groups in N-protected amino acids was measured in order to evaluate the experimental requirements for racemization free cleavages in the absence of strong acid. We are now attempting to apply these techniques during the synthesis of peptides and also involved in selective deprotection of amino acid side-chains. | |
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| Relative Papers |
Online ISSN 1011-6575
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