Competitive binding of peptides containing basic amino acids to disrupt or
prevent the Tat-TAR interaction could result in diminished transcription as
well as translation and hence constitutes an alternative way of controllin
g HN replication. Therefore, we synthesized guanidinium and amino containin
g amino acids, based on a proline or an alanine scaffold. The introduction
of the guanidinium moiety was best accomplished using 1H-pyrazole-1-carboxa
midine hydrochloride, with Pmc used for its protection. The absence of race
mization, maintained throughout the whole synthesis, was confirmed by chira
l purity determination. These building blocks were smoothly incorporated in
to oligopeptides, which proved their suitability for use in a combinatorial
approach for selecting TAR binding ligands. (C) 2000 Elsevier Science Ltd.
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