15446-43-2Relevant articles and documents
Aminoglycoside antibiotic derivatives: Preparation and evaluation of toxicity on cochlea and vestibular tissues and antimicrobial activity
da Silva, Julierme G.,Hyppolito, Miguel A.,de Oliveira, Jose Antonio A.,Corrado, Alexandre P.,Ito, Izabel Y.,Carvalho, Ivone
, p. 3624 - 3634 (2007)
Aminoglycoside antibiotic derivatives such as neamine, methyl neobiosaminide B, 2-deoxystreptamine, tetra-azidoneamine, tetra-N-acetylneamine, tetra-N-carboxy-benzylneamine, tetra-N-carboxy-methylneamine and tetra-p-methoxy-benzyliminoneamine were prepare
NMR and amber analysis of the neamine pharmacophore for the design of novel aminoglycoside antibiotics
Andac, Cenk A.,Stringfellow, Thomas C.,Hornemann, Ulfert,Noyanalpan, Ningur
, p. 28 - 41 (2011)
The dependence of the solution structure of neamine on pH was determined by NMR and AMBER molecular dynamics methods at pD 3.3, pD 6.5, and pD 7.4 in D2O at 25 °C. Unlike neamine structures at pD 3.3 and 6.5, which essentially showed only one conformer, slowly exchanging primary, P-state, and secondary, S-state, neamine conformers populated on the NMR time scale at ～80% and ～20%, respectively, were detected at pD 7.4 with kinetic constants kon(P→S) = 1.9771 s-1 and k off(S→P) = 1.1319 s-1. A tertiary, T-state, neamine species populated at ～3% was also detected by NMR at pD 7.4. The pKa values determined by NMR titration experiments are pKa1 6.44 ± 0.13 for N3 of ring-II, pKa2 7.23 ± 0.09 for N2′ of ring-I, pKa3 7.77 ± 0.19 for N1 of ring-II, and pKa4 8.08 ± 0.15 for N6′ of ring-I. Ring-I and ring-II of the P-state neamine and ring-I of the S and T-states of neamine possess the 4C1 chair conformation between pD 3.3 and pD = 7.4. In contrast, ring-II of the S and T-states of neamine most likely adopt the 6rH1 half-chair conformation. The P and S-states of neamine exhibit a negative syn-ψ glycosidic geometry. The exocyclic aminomethyl group of ring-I adopts the gt exocyclic rotamer conformation around physiological pHs while the gg exocyclic rotamer conformation predominates in acidic solutions near and below pH 4.5. Neamine exists in the P-state as a mixture of tetra-/tri-/di-protonated species between pD 4.5 and pD 7.4, while the S-state neamine exist only in a di-protonated species around physiological pDs. The existence of the S-state neamine may facilitate binding of neamine-like aminoglycosides by favorable entropy of binding to the A-site of 16S ribosomal RNA, suggesting that novel aminoglycoside compounds carrying a S-state neamine pharmacophore can be developed.
Designed spiro-bicyclic analogues targeting the ribosomal decoding center
Cottin, Thomas,Pyrkotis, Constantina,Stathakis, Christos I.,Mavridis, Ioannis,Katsoulis, Ioannis A.,Anastasopoulou, Panoula,Kythreoti, Georgia,Zografos, Alexandros L.,Nahmias, Victoria R.,Papakyriakou, Athanasios,Vourloumis, Dionisios
supporting information; experimental part, p. 71 - 87 (2011/12/16)
The bacterial ribosome represents the confirmed biological target for many known antibiotics that interfere with bacterial protein synthesis. Aminoglycosides represent a lead paradigm in RNA molecular recognition and constitute ideal starting points for t
A short and scalable route to orthogonally O-protected 2-deoxystreptamine
Van Den Broek, Sebastiaan A. M. W.,Gruijters, Bas W. T.,Rutjes, Floris P. J. T.,Van Delft, Floris L.,Blaauw, Richard H.
, p. 3577 - 3580 (2008/02/04)
(Chemical Equation Presented) A seven-step synthesis of orthogonally O-protected 2-deoxy-streptamine has been developed from readily available neomycin, with an overall yield of 28%. Key chemical transformations include a chemoselective glycosidic bond hy
Synthesis of aminoglycoside-modified oligonucleotides
Tona, Rolf,Bertolini, Reto,Hunziker, Juerg
, p. 1693 - 1696 (2007/10/03)
(matrix presented) To study the structural requirements of aminoglycoside binding to nucleic acids, compound 1 - an analogue of the naturally occurring nucleoside J - was synthesized. When incorporated into oligodeoxynucleotides, 1 leads to thermal stabil
