Oligomerizations of various amino acid N-carboxyanhydrides (NCAs) were prepared in the presence of L-tyrosine methyl ester (Tyr.Me). Tyr.Me was found to be an efficient initiator to form oligopeptides consisting of L-aspartic acid, L-glutamic acid, L-phenylalanine, and L-tyrosine with random arrangements of amino acids. In acidic solution, the oligopeptides formed microspheres which were capable of encapsulating macromolecular drugs such as insulin and heparin. These microspheres were considered to be potential oral drug delivery systems.
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