A new class of branched aminoglycosides: Pseudo- pentasaccharide derivatives of neomycin B

被引：53

作者：

Fridman, M ^{[1
]}

Belakhov, V

Yaron, S

Baasov, T

机构：

[1] Technion Israel Inst Technol, Dept Chem, IL-32000 Haifa, Israel

[2] Technion Israel Inst Technol, Inst Catalysis Sci & Technol, IL-32000 Haifa, Israel

[3] Technion Israel Inst Technol, Dept Food Engn & Biotechnol, IL-32000 Haifa, Israel

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 20期

关键词：

D O I：

10.1021/ol035213i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The clinically important antibiotic neomycin B was modified at position C5" by adding one extra sugar ring in the beta-configuration, and the observed pseudo-pentasaccharides were tested against various bacterial strains, including pathogenic and resistant strains. The designed antibiotics show antibacterial activity superior to that of neomycin B against pathogenic and resistant bacterial strains.

引用

页码：3575 / 3578

页数：4

共 27 条

[1] 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

[2] 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

[3] MECHANISM OF BACTERICIDAL ACTION OF AMINOGLYCOSIDES [J].

DAVIS, BD .

MICROBIOLOGICAL REVIEWS, 1987, 51 (03) :341-350

[4] Substrate promiscuity of an aminoglycoside antibiotic resistance enzyme via target mimicry [J].

Fong, DH ;

Berghuis, AM .

EMBO JOURNAL, 2002, 21 (10) :2323-2331

[5] SYNTHESIS OF PSEUDOTRISACCHARIDES RELATED TO RIBOSTAMYCIN [J].

GIRODEAU, JM ;

PINEAU, R ;

MASSON, M ;

LEGOFFIC, F .

JOURNAL OF ANTIBIOTICS, 1984, 37 (02) :150-158

[6] Design and synthesis of new aminoglycoside antibiotics containing neamine as an optimal core structure: Correlation of antibiotic activity with in vitro inhibition of translation [J].

Greenberg, WA ;

Priestley, ES ;

Sears, PS ;

Alper, PB ;

Rosenbohm, C ;

Hendrix, M ;

Hung, SC ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6527-6541

[7] Sequence and characterization of a novel chromosomal aminoglycoside phosphotransferase gene, aph(3')-IIb, in Pseudomonas aeruginosa [J].

Hachler, H ;

Santanam, P ;

Kayser, FH .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1996, 40 (05) :1254-1256

[8] Design of novel antibiotics that bind to the ribosomal acyltransfer site [J].

Haddad, J ;

Kotra, LP ;

Llano-Sotelo, B ;

Kim, C ;

Azucena, EF ;

Liu, MZ ;

Vakulenko, SB ;

Chow, CS ;

Mobashery, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (13) :3229-3237

[9] Synthetic ribofuranose-containing polymers show catalytic activity in the hydrolysis of phosphodiesters [J].

Han, MJ ;

Yoo, KS ;

Cho, TJ ;

Chang, JY ;

Cha, YJ ;

Nam, SH .

CHEMICAL COMMUNICATIONS, 1997, (02) :163-164

[10] The catalytic activity of ribose-containing polymers for the hydrolysis of phosphodiester and the cleavage of nucleic acid [J].

Han, MJ ;

Yoo, KS ;

Kim, YH ;

Chang, JY .

TETRAHEDRON LETTERS, 2002, 43 (32) :5597-5600

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