Synthesis of Alanine and Proline Amino Acids with Amino or Guanidinium Substitution on the Side Chain

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 controlling HIV replication. Therefore, we synthesized guanidinium and amino containi...

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Bibliographic Details
Published in:Tetrahedron 2000-04, Vol.56 (16), p.2513-2522
Main Authors: Zhang, Zhenyu, Aerschot, Arthur Van, Hendrix, Chris, Busson, Roger, David, Frank, Sandra, Pat, Herdewijn, Piet
Format: Article
Language:English
Subjects:
guanidinium substitution
HIV replication
Tat–TAR interaction
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Summary: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 controlling HIV replication. Therefore, we synthesized guanidinium and amino containing amino acids, based on a proline or an alanine scaffold. The introduction of the guanidinium moiety was best accomplished using 1 H-pyrazole-1-carboxamidine hydrochloride, with Pmc used for its protection. The absence of racemization, maintained throughout the whole synthesis, was confirmed by chiral purity determination. These building blocks were smoothly incorporated into oligopeptides, which proved their suitability for use in a combinatorial approach for selecting TAR binding ligands.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00123-X