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Tuning the regioselectivity of the Staudinger reaction for the facile synthesis of kanamycin and neomycin class antibiotics with N-1 modification.
[reaction: see text] A novel method for achieving the desired regioselective reduction of the N-1 azido group on a tetraazidoneamine has been developed that leads to the synthesis of both kanamycinExpand
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Glycodiversification for the optimization of the kanamycin class aminoglycosides.
  • J. Wang, J. Li, +5 authors C. Chang
  • Chemistry, Medicine
  • Journal of medicinal chemistry
  • 2 September 2005
In an effort to optimize the antibacterial activity of kanamycin class aminoglycoside antibiotics, we have accomplished the synthesis and antibacterial assay of new kanamycin B analogues. AExpand
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Conversion of a dodecahedral protein capsid into pentamers via minimal point mutations.
Protein self-assembly relies upon the formation of stabilizing noncovalent interactions across subunit interfaces. Identifying the determinants of self-assembly is crucial for understandingExpand
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In-Depth Comparison of Lysine-Based Antibody-Drug Conjugates Prepared on Solid Support Versus in Solution
Antibody drug conjugates are a rapidly growing form of targeted chemotherapeutics. As companies and researchers move to develop new antibody–drug conjugate (ADC) candidates, high-throughput methodsExpand
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Investigation of the regioselectivity for the staudinger reaction and its application for the synthesis of aminoglycosides with N-1 modification.
The criteria for controlling the regioselectivity of Staudinger reduction of azides have been investigated. These findings enable a convenient direct N-1 modification of the perazidoneamine andExpand
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Biophysical Properties and Heating-Induced Aggregation of Lysine-Conjugated Antibody-Drug Conjugates.
The commercially available antibody-drug conjugate (ADC) product, Kadcyla® is synthesized using a 2-step reaction, wherein the linker is conjugated to native lysines on the mAb in step 1, followed byExpand
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Novel Method for the Synthesis of 3′,4′‐Dideoxygenated Pyranmycin and Kanamycin Compounds, and Studies of Their Antibacterial Activity Against Aminoglycoside‐Resistant Bacteria
A novel protocol for converting a trans‐diol to an alkene under mild conditions was developed. This method led to the synthesis of a 3′,4′‐dideoxykanamycin (dibekacin) analog and aExpand
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Design and synthesis of pyrankacin: a pyranmycin class of broad-spectrum aminoglycoside antibiotic.
A novel broad-spectrum aminoglycoside antibiotic, pyrankacin, has been prepared. In addition to the synthetic innovation in dideoxygenation and regioselective Staudinger reduction, we have obtainedExpand
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Synthesis and antibacterial activity of pyranmycin derivatives with N-1 and O-6 modifications.
Continuing from our ongoing effort in modifying aminoglycoside antibiotics with the goal of counteracting drug resistant bacteria, we have further derivatized pyranmycin, a neomycin classExpand
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