5 research outputs found
Importance of Co-operative Hydrogen Bonding in the Apramycin-Ribosomal Decoding A-Site Interaction
An intramolecular hydrogen bond between the protonated equatorial 7'-methylamino group of apramycin and the vicinal axial 6'-hydroxy group acidifies the 6'-hydroxy group leading to a strong hydrogen bond to A1408 in the ribosomal drug binding pocket in the decoding A site of the small ribosomal subunit. In 6'-epiapramycin, the trans-nature of the 6'-hydroxy group and the 7'-methylamino group results in a much weaker intramolecular hydrogen bond, and a consequently weaker cooperative hydrogen bonding network with A1408, resulting overall in reduced inhibition of protein synthesis and antibacterial activity
One-Step TEMPO-Catalyzed and Water-Mediated Stereoselective Conversion of Glycals into 2‑Azido-2-deoxysugars with a PIFA–Trimethylsilyl Azide Reagent System
An unprecedented water-mediated and
TEMPO-catalyzed, one-step,
highly regiospecific and stereoselective functionalization of glycals
to 2-azido-2-deoxysugars has been developed using a PIFA–Me<sub>3</sub>SiN<sub>3</sub> reagent system in the presence of Bu<sub>4</sub>NHSO<sub>4</sub> as a phase-transfer catalyst. The method is metal-free,
proceeds under mild reaction conditions, and tolerates a variety of
protecting groups. Using this method, the synthesis of an important
trisaccharide unit bound by the monoclonal anti-I Ma antibody has
also been demonstrated
Importance of Co-operative Hydrogen Bonding in the Apramycin-Ribosomal Decoding A-Site Interaction
An intramolecular hydrogen bond between the protonated equatorial 7’-methylamino group of apramycin and the vicinal axial 6’-hydroxy group acidifies the 6’-hydroxy group leading to a strong hydrogen bond to A1408 in the ribosomal drug binding pocket in the decoding A site of the small ribosomal subunit. In 6’-epiapramycin, the trans-nature of the 6’-hydroxy group and the 7’-methylamino group results in a much weaker intramolecular hydrogen bond, and a consequently weaker cooperative hydrogen bonding network with A1408, resulting overall in reduced inhibition of protein synthesis and antibacterial activity.ISSN:1860-7179ISSN:1860-718