Side reactions in peptide synthesis. VII. Sequence dependence in the formation of aminosuccinyl derivatives from beta-benzyl-aspartyl peptides.
The base catalyzed ring closure in t-Boc-Asp-X beta-napthylamides was examined in a series of 2-peptide derivatives in which position X was occupied by the neutral and acidic amino acid residues that occur in proteins. Bulkiness and functional groups in the side chain of X have a major effect on the rate of cyclization, e.g. acidic groups slow down the formation of aminosuccinyl derivatives. Rate-enhancing effect can be observed in serine and threonine, while the side reaction is unexpectedly slow when X is methionine.
D000596:Amino Acids; D001224:Aspartic Acid; D001593:Benzyl Compounds; D055598:Chemical Phenomena; D002621:Chemistry; D008722:Methods; D010455:Peptides / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D013386:Succinates
D000596:Amino Acids; D001593:Benzyl Compounds; D010455:Peptides; D013386:Succinates; D001224:Aspartic Acid