Novel 2,5-dideoxystreptamine derivatives targeting the ribosomal decoding site RNA

被引：43

作者：

Vourloumis, D

Takahashi, M

Winters, GC

Simonsen, KB

Ayida, BK

Barluenga, S

Qamar, S

Shandrick, S

Zhao, Q

Hermann, T

机构：

[1] Anadys Pharmaceut Inc, Dept Med Chem, San Diego, CA 92121 USA

[2] Anadys Pharmaceut Inc, Dept RNA Biochem, San Diego, CA 92121 USA

[3] Anadys Pharmaceut Inc, Dept Computat Chem & Struct, San Diego, CA 92121 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2002年 / 12卷 / 23期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0960-894X(02)00759-X

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The ribosomal decoding site is the target of aminoglycoside antibiotics that specifically recognize an internal loop RNA structure. We synthesized RNA-targeted 2,5-dideoxystreptamine-4-amides in which a sugar moiety in natural aminoglycosides is replaced by heterocycles. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：3367 / 3372

页数：6

相关论文

共 46 条

[1] Metal catalyzed diazo transfer for the synthesis of azides from amines [J].

Alper, PB ;

Hung, SC ;

Wong, CH .

TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032

[2] Probing the specificity of aminoglycoside ribosomal RNA interactions with designed synthetic analogs [J].

Alper, PB ;

Hendrix, M ;

Sears, P ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (09) :1965-1978

[3] SYNTHESIS OF DEOXYHALOGENO SUGARS - DISPLACEMENT OF THE (TRIFLUOROMETHANESULFONYL)OXY (TRIFLYL) GROUP BY HALIDE ION [J].

BINKLEY, RW ;

AMBROSE, MG ;

HEHEMANN, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (22) :4387-4391

[4] The structural basis for the action of the antibiotics tetracycline, pactamycin, and hygromycin B on the 30S ribosomal subunit [J].

Brodersen, DE ;

Clemons, WM ;

Carter, AP ;

Morgan-Warren, RJ ;

Wimberly, BT ;

Ramakrishnan, V .

CELL, 2000, 103 (07) :1143-1154

[5] Functional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics [J].

Carter, AP ;

Clemons, WM ;

Brodersen, DE ;

Morgan-Warren, RJ ;

Wimberly, BT ;

Ramakrishnan, V .

NATURE, 2000, 407 (6802) :340-348

[6] TRIFLUOROMETHANESULFONYL AZIDE - ITS REACTION WITH ALKYL AMINES TO FORM ALKYL AZIDES [J].

CAVENDER, CJ ;

SHINER, VJ .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (22) :3567-&

[7] An efficient synthesis of mimetics of neamine for RNA recognition [J].

Ding, YL ;

Hofstadler, SA ;

Swayze, EE ;

Griffey, RH .

ORGANIC LETTERS, 2001, 3 (11) :1621-1623

[8] Binding of neomycin-class aminoglycoside antibiotics to the A-site of 16 S rRNA [J].

Fourmy, D ;

Recht, MI ;

Puglisi, JD .

JOURNAL OF MOLECULAR BIOLOGY, 1998, 277 (02) :347-362

[9] Paromomycin binding induces a local conformational change in the A-site of 16 S rRNA [J].

Fourmy, D ;

Yoshizawa, S ;

Puglisi, JD .

JOURNAL OF MOLECULAR BIOLOGY, 1998, 277 (02) :333-345

[10] Structure of the A site of Escherichia coli 16S ribosomal RNA complexed with an aminoglycoside antibiotic [J].

Fourmy, D ;

Recht, MI ;

Blanchard, SC ;

Puglisi, JD .

SCIENCE, 1996, 274 (5291) :1367-1371

← 1 2 3 4 5 →