Title: Synthesis of alanine and proline amino acids with amino or guanidinium substitution on the side chain
Authors: Zhang, Zhenyu ×
Van Aerschot, Arthur
Hendrix, Christel
Busson, Roger
David, F
Sandra, P
Herdewijn, Piet #
Issue Date: 2000
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:56 issue:16 pages:2513-2522
Abstract: 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 HN 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 1H-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. (C) 2000 Elsevier Science Ltd. All rights reserved.
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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