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Acid-Mediated Prevention of Aspartimide Formation in Solid Phase Peptide Synthesis
Tillmann Michels, Rudolf Dölling, Uwe Haberkorn, and Walter Mier
Org. Lett., Article ASAP
DOI: 10.1021/ol3007925
Publication Date (Web): October 1, 2012
Copyright © 2012 American Chemical Society

Aspartimide formation is one of the major obstacles that impedes the solid phase synthesis of large peptides and proteins. Until now, no cost-effective strategy to suppress this side reaction has been developed. Here it is demonstrated that addition of small amounts of organic acids to the standard Fmoc cleavage agent piperidine efficiently prevents formation of aspartimide side products. This effect is shown to be virtually independent of the acid strength.