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An efficient mild acidolytic deprotection procedure for Boc/Bzl-based solid phase peptide synthesis

1990; Wiley-VCH; Volume: 55; Issue: 7 Linguagem: Inglês

10.1135/cccc19901792

1212-6950

R. Dölling, Peter Jeschke, Albrecht Otto, Jutta Eichler,

Carbohydrate Chemistry and Synthesis

Using the mild acidolytic deprotecting reagents 0.1M MSA or 0.1M TMSOTf in TFA in combination with PMB, which simultaneously accelerates the cleavage and acts as irreversible scavenger, the rate of cleavage of a model dipeptide from the appropriate N α -Fmoc-dipeptidyl resin (polymer-bound benzyl ester, p -MBHA and BHA resin, respectively) was studied. The new deprotecting method was successfully applied to the synthesis of three N α -halogenoacetyl modified octapeptides ( I, II ) and a 16-residue peptide ( III ). In all cases, the crude products were of the same quality as peptides obtained via the HF/10% anisole technique.