TY - JOUR
T1 - A valuable synthesis of reduced peptide bond by microwave irradiation
AU - Santagada, Vincenzo
AU - Frecentese, Francesco
AU - Fiorino, Ferdinando
AU - Cirillo, Donatella
AU - Perissutti, Elisa
AU - Severino, Beatrice
AU - Terracciano, Sara
AU - Caliendo, Giuseppe
PY - 2004/12
Y1 - 2004/12
N2 - 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.
AB - 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.
KW - Microwave irradiation
KW - Surrogate peptide bond
KW - Synthesis of CHNH group
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U2 - 10.1002/qsar.200420037
DO - 10.1002/qsar.200420037
M3 - Article
AN - SCOPUS:12344330343
VL - 23
SP - 899
EP - 901
JO - QSAR and Combinatorial Science
JF - QSAR and Combinatorial Science
SN - 1611-020X
IS - 10
ER -