The crystal structure of kanamycin

Koyama, Gunji; Iitaka, Yōichi; Maeda, Kenji; Umezawa, Hamao

doi:10.1016/s0040-4039(00)76384-2

Cited by 37 publications

(10 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The 4‘‘- and 2‘‘-hydroxyls are vicinal to the 3‘‘-amino group. Additionally, the 2‘‘-OH is within a hydrogen-bonding distance from the 1-amino group on the 2-deoxystreptamine ring . Therefore, removal of the 4‘- or the 4‘‘-hydroxyl may enhance the basicity of the corresponding neighboring amine group, while deoxygenation of the 2‘‘-hydroxyl may affect two amino groups simultaneously, supporting the superior inhibitory activity observed for 6 .…”

mentioning

confidence: 79%

Electrostatic Interactions in RNA Aminoglycosides Binding

1997

View full text Add to dashboard Cite

mentioning

confidence: 79%

Electrostatic Interactions in RNA Aminoglycosides Binding

1997

View full text Add to dashboard Cite

“…The crystal structure of kanamycin A shows that all three rings in the molecule assume the chair conforma-tion. 15 Its four amino functions, together with the neighboring hydroxyl groups, offer several potential binding sites for metal ions, such as copper(II), which was previously demonstrated to form stable complexes with related aminoglycosides. [16][17][18][19] Aminosugars bind Cu(II) effectively.…”

Section: Introductionmentioning

confidence: 99%

Copper(ii) binding by kanamycin A and hydrogen peroxide activation by resulting complexes

et al. 2002

View full text Add to dashboard Cite

Protonation and copper(II) coordination properties of kanamycin A were studied in solution by potentiometry, UV-Vis, circular dichroism (CD), EPR and cyclic voltammetry (CV). Only mononuclear complexes of stoichiometries ranging from CuH 2 L to CuH À2 L were found. Kanamycin A anchors Cu(II) ions with an {NH 2 , O À } chelate of the C-ring of its molecule. At pH higher than 6 the amino and hydroxyl groups of the A-ring of kanamycin A also participate in binding. The resulting structure, similar to that of complexes of other unsubstituted aminoglycosides studied previously, involves Cu(II) coordination by donors of terminal aminosugar rings, rather than those of the central unit. The results of cyclic voltammetry investigations, kinetic studies of H 2 O 2 disproportionation and ROS detection experiments, further supported the mechanism of oxidative reactivity of cupric complexes of aminoglycosides, proposed by us recently [M. Jez ˙owska-Bojczuk, W.

show abstract

“…The 1 H NMR spectra of the imines formed at different amine groups were calculated with DFT‐GIAO B3LYP/6‐31G, and the Δ δ of the final conformations were compared with the changes observed in the experimental 1 H spectra. Some structural parameters were also compared with the analogous distances and angles in free km , employing the X‐ray structure as reference …”

Section: Resultsmentioning

confidence: 97%

Kanamycin A: imine formation in aqueous solution

Fuentes-Martínez

Godoy‐Alcántar

Medrano

et al. 2012

J of Physical Organic Chem

View full text Add to dashboard Cite

Imine formation in aqueous solution of kanamycin A with pyridoxal 5'-phosphate and other aldehydes was studied by potentiometry, NMR spectroscopy and computational chemistry. It was found that imines are formed with yields near 100 % at pH 7 in equimolar reactant ratio. In order to identify the kanamycin amino groups involved in the reaction, a NMR spectroscopic study was conducted. The structures of possible imines formed between kanamycin and FURAN or PLP were optimized by molecular mechanics with the OPLS-2005 force field. The 1 H NMR spectra were calculated at the DFT-GIAO B3LYP/6-31G(d) level of theory for all structures and compared with the experimentally observed spectra. From these results a probable structure of the imines was proposed. The results obtained in this work show that kanamycin has the ability to form imine derivatives in high yields due to its anion recognition properties.

show abstract

The crystal structure of kanamycin

Cited by 37 publications

References 3 publications

Electrostatic Interactions in RNA Aminoglycosides Binding

Electrostatic Interactions in RNA Aminoglycosides Binding

Copper(ii) binding by kanamycin A and hydrogen peroxide activation by resulting complexes

Kanamycin A: imine formation in aqueous solution

Contact Info

Product

Resources

About