Synthesis of alanine and proline amino acids with amino or guanidinium substitution on the side chain

Citation
Zy. Zhang et al., Synthesis of alanine and proline amino acids with amino or guanidinium substitution on the side chain, TETRAHEDRON, 56(16), 2000, pp. 2513-2522
Citations number
25
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
0040-4020 → ACNP
Volume
56
Issue
16
Year of publication
2000
Pages
2513 - 2522
Database
ISI
SICI code
0040-4020(20000414)56:16<2513:SOAAPA>2.0.ZU;2-L
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 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. All rights reserved.