T. Kaneko, I. Takeuchi, T. Inui
Apr 1, 1968
Citations
0
Influential Citations
14
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The treatment of N-benzyloxycarbonyl-L-alanyl-L-serine methyl ester (I) with phosgene afforded the corresponding O-chlorocarbonyl derivative (II), which was then cyclized to methyl L-3-(N-benzyloxycarbonyl-L-alanyl)-2-oxo-oxazolidine-4-carboxylate (III) accompanied with N-benzyloxycarbonyl-L-alanyl-3-chloro-L-alanine methyl ester (IV) by refluxing in xylene. By the mild alkaline hydrolysis of III, N-benzyloxycarbonyl-L-alanine and L-2-oxo-oxazolidine-4-carboxylic acid (V) were isolated as a result of the selective cleavage of the peptide bond in which an amino group of the serine residue participated. This method was also applied to three other serine peptides; the same results were obtained.