Selective deprotection of the Cbz amine protecting group for the facile synthesis of kanamycin A dimers linked at N-3″ position

Chen, Guihui; Pan, Pan; Chen, Ying; Meng, Xiangbao; Li, Zhongjun

doi:10.1016/j.tet.2009.06.002

Cited by 9 publications

(3 citation statements)

References 17 publications

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“…The lack of improved activity is in contrast to findings by other groups [ 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 ], which may be explained in our case by the relatively short linkers employed. It is not excluded that a short linker is precluding cooperative binding of the other end of the molecule to a second binding pocket.…”

Section: Resultscontrasting

confidence: 99%

“…However, neamine still contains the diaminosugar ring I of aminoglycosides, and is therefore a substrate for several resistance enzymes. Dimeric aminoglycoside have also divulged an improved RNA binding than individual aminoglycosides [ 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 ], therefore we made the dimers of our conjugates with conformationally adaptable linkers to further enhance binding affinity. These compounds were then tested for antibacterial activity against E. coli with a fluorescence-based assay.…”

Section: Introductionmentioning

confidence: 99%

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2-Deoxystreptamine Conjugates by Truncation–Derivatization of Neomycin

et al. 2010

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A small library of truncated neomycin-conjugates is prepared by consecutive removal of 2,6-diaminoglucose rings, oxidation-reductive amination of ribose, oxidation-conjugation of aminopyridine/aminoquinoline and finally dimerization. The dimeric conjugates were evaluated for antibacterial activity with a unique hemocyanin-based biosensor. Based on the outcome of these results, a second-generation set of monomeric conjugates was prepared and found to display significant antibacterial activity, in particular with respect to kanamycin-resistant E. coli.

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Section: Resultscontrasting

confidence: 99%

Section: Introductionmentioning

confidence: 99%

2-Deoxystreptamine Conjugates by Truncation–Derivatization of Neomycin

et al. 2010

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“…Aminoglycosides are a group of natural antibiotics from Streptomyces that have been used in clinical practice for more than 50 years [ 4 ]. Their potent bactericidal activity relies upon binding specifically to the 16S rRNA of the 30S ribosomal subunit, thus interfering with protein synthesis [ 5 , 6 ]. However, the first resistant bacterial strains began to appear in the 1960s due to a high rate of dissemination via R-plasmids, transposons, and integrons [ 7 , 8 ].…”

Section: Introductionmentioning

confidence: 99%

Overcoming Aminoglycoside Enzymatic Resistance: Design of Novel Antibiotics and Inhibitors

et al. 2018

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Resistance to aminoglycoside antibiotics has had a profound impact on clinical practice. Despite their powerful bactericidal activity, aminoglycosides were one of the first groups of antibiotics to meet the challenge of resistance. The most prevalent source of clinically relevant resistance against these therapeutics is conferred by the enzymatic modification of the antibiotic. Therefore, a deeper knowledge of the aminoglycoside-modifying enzymes and their interactions with the antibiotics and solvent is of paramount importance in order to facilitate the design of more effective and potent inhibitors and/or novel semisynthetic aminoglycosides that are not susceptible to modifying enzymes.

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Protection for the Amino Group

2014

Greene's Protective Groups in Organic Synthesis

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CARBAMATES 907Carbamate Derived from an Amine and CO 2 , 908 Methyl and Ethyl, 909 9-Fluorenylmethyl, 912 2,6-Di-t-butyl-9-fluorenylmethyl, 915 2,7-Bis (trimethylsilyl)fluorenylmethyl, 915 2-(2-Ethylhexyl)-9-fluorenylmethyl, 915 2,7-Bis-(2-ethylhexyl)-9-fluorenylmethyl, 915 9-(2-Sulfo)fluorenylmethyl, 916 9-(2,7-Dibromo)fluorenylmethyl, 916 17-Tetrabenzo[a,c,g,i]fluorenylmethyl, 916 2-Chloro-3-indenylmethyl, 916 Benz[f]inden-3-ylmethyl, 916 1,1-Dioxobenzo[b]thiophene-2-ylmethyl, 917 2,7-Di-t-butyl[9-(10,10-dioxo-10,10,10,10-tetrahydrothioxanthyl)]methyl, 917 Azidomethyl, 920 2-(Hydroxymethyl)-3-phenyl-4H-1-benzothiopyran-4-one 1,1-Dioxide, 920 2-Methylsulfonyl-3-phenyl-1-prop-2-enyloxy, 920 Substituted Ethyl Carbamates 921 2,2,2-Trichloroethyl, 921 2-Trimethylsilylethyl, 923 (2-Phenyl-2-trimethylsilyl)ethyl, 925 2-(Triphenylsilyl)ethyl, 925 2-Phenylethyl, 927 2-Chloroethyl, 927 2 3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decyl, 927 1,1-Dimethyl-2-haloethyl, 927 1,1-Dimethyl-2,2-dibromoethyl, 927 1,1-Dimethyl-2,2,2-trichloroethyl, 928 2-(2´and 4´-Pyridyl)ethyl, 928

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Selective deprotection of the Cbz amine protecting group for the facile synthesis of kanamycin A dimers linked at N-3″ position

Cited by 9 publications

References 17 publications

2-Deoxystreptamine Conjugates by Truncation–Derivatization of Neomycin

2-Deoxystreptamine Conjugates by Truncation–Derivatization of Neomycin

Overcoming Aminoglycoside Enzymatic Resistance: Design of Novel Antibiotics and Inhibitors

Protection for the Amino Group

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