Click-chemistry-derived tetracycline-amino acid conjugates exhibiting exceptional potency and exclusive recognition of the reverse tet repressor.
Chembiochem
; 11(5): 703-12, 2010 Mar 22.
Article
em En
| MEDLINE
| ID: mdl-20148427
ABSTRACT
A click-chemistry-based synthesis of biologically active doxycycline-amino acid conjugates is described. Starting from 9-aminodoxycycline derivatives and complementary functionalized amino acids, ligation was accomplished by copper(I)-catalyzed azide-alkyne [3+2] cycloaddition (CuAAC). The final products were tested in a variety of TetR and revTetR systems, and the C-terminally linked phenylalanine conjugate 12 c exhibited high selectivity for revTetR over TetR. Besides the unique property of the specific effector 12 c to effectively differentiate TetR and its reverse phenotype, the test compound proved to be almost devoid of any antibacterial activity; this will be highly beneficial for future applications to control gene expression in bacterial systems.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Fenilalanina
/
Proteínas Repressoras
/
Doxiciclina
/
Aminoácidos
Idioma:
En
Ano de publicação:
2010
Tipo de documento:
Article