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The conjugation of peptides and proteins to poly(aminoamide)s with PNA building blocks is of special interest because of the possibility to introduce additional functional groups at the termini of these compounds. In this study, amino acids were conjugated to the nitrogen atom of the backbone of the PNA by linking them to the alpha position of the N-terminal amino group. Three sets of 14-mer PNA analogs were synthesized by phosphoramidite chemistry. One set consisted of N-terminal linked amino acids (alanine, valine, isoleucine, phenylalanine, proline, and threonine), the second set consisted of C-terminal linked amino acids (alanine, valine, leucine, phenylalanine, and threonine) and the third set of PNA analogs contained non-natural amino acids (2-aminobutyric acid, 2-aminoadipic acid, phenylalanine 3,5-diacetate, and phenylalanine 4-acetate). The purity of the PNA analogs was tested by HPLC and the molecular mass was checked by MALDI-TOF mass spectrometry. A good correlation (R(2)=0.971) was established between the theoretical and the experimentally determined molecular masses. Conjugation of an amino