NMR-Guided fragment-based approach for the design of tRNALys3 ligands

被引：37

作者：

Chung, Florence ^{[1
]}

Tisne, Carine ^{[1
]}

Lecourt, Thomas ^{[1
]}

Dardel, Frederic ^{[1
]}

Micouin, Laurent ^{[1
]}

机构：

[1] Univ Paris 05, CNRS, Cristallogr & RMN Biol, F-75006 Paris, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 24期

关键词：

aminoglycoside mimics; drug design; fragment-based synthesis; RNA recognition; tRNA;

D O I：

10.1002/anie.200605201

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two in one: Two ligands for tRNALys3 that were identified from a compound library by flow-injection NMR spectroscopic screening and found to have millimolar dissociation constants (on the left in the picture) inspired the fragment-based synthesis of a new family of ligands with the general structural features of both initial compounds. Ligand 1 of this family is a selective D-stem binder of tRNALys3 with a micromolar Kd value. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4489 / 4491

页数：3

共 27 条

[1]

Begis G., 2006, Patent application WO, Patent No. 2006024784

[2] The crystal structure of HIV reverse-transcription primer tRNA(Lys,3) shows a canonical anticodon loop [J].

Bénas, P ;

Bec, G ;

Keith, G ;

Marquet, R ;

Ehresmann, C ;

Ehresmann, B ;

Dumas, P .

RNA, 2000, 6 (10) :1347-1355

[3] Fragment-based drug discovery [J].

Erlanson, DA ;

McDowell, RS ;

O'Brien, T .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (14) :3463-3482

[4] Crystal structures of complexes between aminoglycosides and decoding A site oligonucleotides:: role of the number of rings and positive charges in the specific binding leading to miscoding [J].

François, B ;

Russell, RJM ;

Murray, JB ;

Aboul-ela, F ;

Masquida, B ;

Vicens, Q ;

Westhof, E .

NUCLEIC ACIDS RESEARCH, 2005, 33 (17) :5677-5690

[5] tRNAPhe binds aminoglycoside antibiotics [J].

Kirk, SR ;

Tor, Y .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (09) :1979-1991

[6] Deoxystreptamine dimers bind to RNA hairpin loops [J].

Liu, XJ ;

Thomas, JR ;

Hergenrother, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9196-9197

[7]

Luedtke N W, 2003, SMALL MOL DNA RNA BI

[8] Enantio selective desymmetrization of meso bicyclic hydrazines: A novel approach to the asymmetric synthesis of polysubstituted amino cyclopentanic cores [J].

Luna, AP ;

Ceschi, MA ;

Bonin, M ;

Micouin, L ;

Husson, HP ;

Gougeon, S ;

Estenne-Bouhtou, G ;

Marabout, B ;

Sevrin, M ;

George, P .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) :3522-3524

[9] Reversal of enantioselectivity in the asymmetric rhodium- versus iridium-catalyzed hydroboration of meso substrates [J].

Luna, AP ;

Bonin, M ;

Micouin, L ;

Husson, HP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (41) :12098-12099

[10] TRANSFER-RNAS AS PRIMER OF REVERSE TRANSCRIPTASES [J].

MARQUET, R ;

ISEL, C ;

EHRESMANN, C ;

EHRESMANN, B .

BIOCHIMIE, 1995, 77 (1-2) :113-124

← 1 2 3 →