Methyleneamine is a reduced form of the amide bond. The CH2NH group may be a useful tool for delineating important hydrogen-bonding points and may also offer a general strategy for the production of enzyme resistance and potent competitive antagonists. This paper describes a facile synthesis of the CH2NH group by application of microwave energy. Moreover the importance of sterically hindered amino acids as well as the electronic effects of the side chain, in the synthesis of the hydroxamate and in the reductive alkylation steps, are evaluated. Room temperature, conventional heating and microwave irradiation of the reactions are compared. Synthesis by microwave irradiation gave the desired compound in higher yields and in shorter reaction times than those obtained at room temperature.
- Microwave irradiation
- Surrogate peptide bond
- Synthesis of CHNH group
ASJC Scopus subject areas
- Discrete Mathematics and Combinatorics