Selective, On-Resin N-Methylation of Peptide N-Trifluoroacetamides
2013
Turner, Rushia A. | Hauksson, Niels E. | Gipe, Jordan H. | Lokey, R Scott
Mild and efficient methods for site-specific methylation of peptide backbone amides are important tools for chemists seeking to modulate the pharmacokinetic properties of peptide drugs. The Mitsunobu reaction was used to selectively methylate N-trifluoroacetamide (Tfa) protected peptides on-resin. The Tfa group was removed quickly and completely by reduction with excess NaBH₄, and it was shown to be orthogonal to many of the protecting groups used in solid-phase peptide synthesis.
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