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A facile strategy to prevent trifluoroacetylation of N-terminal proline peptides
Authors:Christian HaaseMatthew F. Burton  Stijn M. AgtenLuc Brunsveld
Affiliation:Laboratory of Chemical Biology, Department of Biomedical Engineering, Eindhoven University of Technology, Den Dolech 2, 5612AZ Eindhoven, The Netherlands
Abstract:Unwanted trifluoroacetylation occurred at the N-terminus of prolinyl peptides during detachment from the solid phase. This was observed when the N-α-Fmoc protecting group had been removed prior to the final TFA treatment. Subtly changing the SPPS protocol and incorporating Boc- in place of the Fmoc-protected proline as the N-terminal building block efficiently suppressed this side reaction.
Keywords:Solid-phase peptide synthesis   N-terminal proline   Modification   Trifluoroacetylation
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