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One challenge facing peptide synthesis is the -lactam formation of arginine （Figure 1）. The formation of -lactam occurs when the internal nitrogen of the guanidine attacks the activated ester, irreversibly forming the lactam ring. This reaction is competitive with peptide-bond formation, greatly reducing the coupling efficiency of arginine.
Figure 1: γ-Lactam Formation
The goal of this study was to determine what effect microwave irradiation has on -lactam formation and how to optimize the microwave synthesis of arginine-containing peptides. As a test substrate, we selected the 1992 ABRF study peptide sequence. This sequence is known to suffer from Arg deletion due to -lactam formation.
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