Microwave Assisted SPPS of Hindered, Non-Standard Amino Acids

Introduction

Hindered, non-standard amino acids such as α-aminoisobutyric acid (Aib) and N-methyl alanine ((N-Me)-A) (Figure 1) can be found in many biologically relevant compounds. The synthesis of peptides including Aib or N-methylated amino acids has proved challenging, however; the steric hindrance introduced by the second methyl group, whether on the α-carbon or the amide nitrogen, makes coupling these amino acid derivatives difficult in conventional SPPS.

Figure 1.  Sterically-hindered, non-standard amino acids

Through the use of microwave-enhanced SPPS, though, difficulties associated with hindered, non-standard amino acids have been minimized. The employment of microwave energy in SPPS drives conventionally-difficult couplings of bulky amino acids, like Aib and N-methyl alanine, quickly and efficiently to completion.

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