Carbohydrate mimic of 2-deoxystreptamine for the preparation of conformationally constrained aminoglycosides

被引：9

作者：

Busscher, Guuske F. ^{[1
]}

van den Broek, Sebastiaan A. M. W. ^{[1
]}

Rutjes, Floris P. J. T. ^{[1
]}

van Delft, Floris L. ^{[1
]}

机构：

[1] Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands

来源：

TETRAHEDRON | 2007年 / 63卷 / 15期

关键词：

S RIBOSOMAL-RNA; A-SITE; CRYSTAL-STRUCTURE; ANTIBIOTICS; OLIGONUCLEOTIDE; RESISTANCE; NEOMYCIN; BINDING; SPECIFICITY; TOBRAMYCIN;

D O I：

10.1016/j.tet.2007.02.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a carbohydrate mimic of 2-deoxystreptamine (2-DOS) is described starting from D-ribose. Crucial steps of the synthesis involve a stereoselective nitroaldol condensation and deoxygenation via elimination-in situ reduction. Moreover, glycosylation of the carbohydrate 2-DOS derivative with a phenyl thioglycoside donor in the presence of TTBP and AgOTf followed by ring-closing metathesis yielded a conformationally restricted aminoglycoside analogue. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：3183 / 3188

页数：6

共 36 条

[1] A simple structural-based approach to prevent aminoglycoside inactivation by bacterial defense proteins.: Conformational restriction provides effective protection against neomycin-B nucleotidylation by ANT4 [J].

Asensio, JL ;

Hidalgo, A ;

Bastida, A ;

Torrado, M ;

Corzana, F ;

Chiara, JL ;

García-Junceda, E ;

Cañada, J ;

Jiménez-Barbero, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) :8278-8279

[2] CYCLISATIONEN VON DIALDEHYDEN MIT NITROMETHAN .4. DARSTELLUNG VON 3-NITRO-DESOXY-METHYL-BETA-D-HEXOPYRANOSIDEN UND 3-AMINO-3-DESOXY-METHYL-BETA-D-HEXOPYRANOSIDEN [J].

BAER, HH .

CHEMISCHE BERICHTE-RECUEIL, 1960, 93 (12) :2865-2871

[3]

BAER HH, 1963, CAN J CHEM, V410, P1606

[4]

BAER HH, 1972, METHODS CARBOHYDR CH, V6, P245

[5]

BEAUCAIRE G, 1995, J CHEMOTHERAPY, V7, P111

[6] Conformational constraint as a means for understanding RNA-aminoglycoside specificity [J].

Blount, KF ;

Zhao, F ;

Hermann, T ;

Tor, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (27) :9818-9829

[7] 2-deoxystreptamine: Central scaffold of aminoglycoside antibiotics [J].

Busscher, GF ;

Rutjes, FPJT ;

van Delft, FL .

CHEMICAL REVIEWS, 2005, 105 (03) :775-791

[8] 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

[9] 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

[10] 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

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