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
Asensio, JL
Hidalgo, A
Bastida, A
Torrado, M
Corzana, F
Chiara, JL
García-Junceda, E
Cañada, J
Jiménez-Barbero, J
[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
BAER, HH
[J]. 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
Blount, KF
Zhao, F
Hermann, T
Tor, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (27) : 9818 - 9829
[7] 2-deoxystreptamine: Central scaffold of aminoglycoside antibiotics
Busscher, GF
Rutjes, FPJT
van Delft, FL
[J]. CHEMICAL REVIEWS, 2005, 105 (03) : 775 - 791
[8] Functional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics
Carter, AP
Clemons, WM
Brodersen, DE
Morgan-Warren, RJ
Wimberly, BT
Ramakrishnan, V
[J]. NATURE, 2000, 407 (6802) : 340 - 348
[9] Binding of neomycin-class aminoglycoside antibiotics to the A-site of 16 S rRNA
Fourmy, D
Recht, MI
Puglisi, JD
[J]. 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
Fourmy, D
Yoshizawa, S
Puglisi, JD
[J]. JOURNAL OF MOLECULAR BIOLOGY, 1998, 277 (02) : 333 - 345

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