SOLID PHASE SYNTHESIS WITHOUT REPETITIVE ACIDOLYSIS
- 12 January 1979
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 13 (1) , 35-42
- https://doi.org/10.1111/j.1399-3011.1979.tb01847.x
Abstract
The utility of repetitive nonhydrolytic base cleavage of α-amino protective groups in solid phase peptide synthesis is shown by a preparation of the model tetrapeptide leucyl-alanyl-glycyl-valine on a p-benzyloxybenzyl ester polystyrene–1% divinylbenzene resin support. Nα-9-Fluorenylmethyloxycarbonyl (Fmoc: Carpino & Han, 1970, 1972) amino acids were coupled by the symmetrical anhydride procedure, followed by Fmoc group cleavage using 50% piperidine in methylene chloride. Quantitative removal of the Fmoc-tetrapeptide from the solid support was effected by treatment with 55% trifluoroacetic acid in methylene chloride. Homogeneous free tetrapeptide was obtained in 87% overall yield. The procedure is proposed to offer advantages over present solid phase methods which use acidolysis for repetitive α-amino group deblocking.Keywords
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