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Tripeptides from Synthetic Amino Acids Block the Tat–TAR Association and Slow Down HIV Spread in Cell Cultures
Author(s) -
Ludwig Verena,
Krebs Andreas,
Stoll Michaela,
Dietrich Ursula,
Ferner Jan,
Schwalbe Harald,
Scheffer Ute,
Dürner Gerd,
Göbel Michael W.
Publication year - 2007
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200700232
Subject(s) - tripeptide , tar (computing) , amino acid , human immunodeficiency virus (hiv) , chemistry , block (permutation group theory) , biochemistry , combinatorial chemistry , biology , virology , computer science , programming language , geometry , mathematics
Non‐natural amino acids with aromatic or heteroaromatic side chains were incorporated into tripeptides of the general structure Arg‐X‐Arg and tested as ligands of the HIV RNA element TAR. Some of these compounds could compete efficiently with the association of TAR and Tat and downregulated a TAR‐controlled reporter gene in HeLa cells. Peptide 7 , which contains a 2‐pyrimidinyl‐alkyl chain, also inhibited the spread of HIV‐1 in cell cultures. NMR studies of 7 bound to HIV‐2‐TAR gave evidence for contacts in the bulge region.