17460-45-6Relevant articles and documents
Hydrolysis of the GlcNAc oxazoline: deamidation and acyl rearrangement
Jha, Rajesh,Davis, Jeffrey T.
, p. 125 - 134 (1995)
The specific deamidation of 2-acetamido-1,3,4,6-tetra-O-acetyl-α-D-glucopyranose is achieved by p-toluenesulfonic acid-promoted hydrolysis of 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)--2-oxazoline 2 to give quantitative formation of the 1,3,4,6-tetra-O-actyl-2-amino-2-deoxy-α-D-glucopyranose p-toluenosulfonate (5d).This two-step procedure provides an amino sugar which may be readily acylated to give novel glycoconjugates.Altermatively, base-catalyzed O-1 --> N-2 acyl rearrangemet of the amino tosylate 5d gives the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranose 4 as a 9:1 mixture of α and β anomers.Thus, hydrolysis of GlcNAc oxazoline 2 gives the amino-ester 5 as the kinetic product and the amido-alcohol 4 as the thermodynamic product.Keywords: GlcNAc oxazoline; Deamidation; Acyl rearrangement
Design, synthesis and antimicrobial evaluation of novel glycosylated-fluoroquinolones derivatives
Mohammed, Aya A. M.,Okechukwu, Patrick N.,Shehadeh, Mayadah B.,Suaifan, Ghadeer A. R. Y.
, (2020/07/04)
Herein we report the design, synthesis and biological evaluation of structurally modified ciprofloxacin, norfloxacin and moxifloxacin standard drugs, featuring amide functional groups at C-3 of the fluoroquinolone scaffold. In vitro antimicrobial testing against various Gram-positive bacteria, Gram-negative bacteria and fungi revealed potential antibacterial and antifungal activity. Hybrid compounds 9 (MIC 0.2668 ± 0.0001 mM), 10 (MIC 0.1358 ± 00025 mM) and 13 (MIC 0.0898 ± 0.0014 mM) had potential antimicrobial activity against a fluoroquinolone-resistant Escherichia coli clinical isolate, compared to ciprofloxacin (MIC 0.5098 ± 0.0024 mM) and norfloxacin (MIC 0.2937 ± 0.0021 mM) standard drugs. Interestingly, compound 10 also exerted potential antifungal activity against Candida albicans (MIC 0.0056 ± 0.0014 mM) and Penicillium chrysogenum (MIC 0.0453 ± 0.0156 mM). Novel derivatives and standard fluoroquinolone drugs exhibited near-identical cytotoxicity levels against L6 muscle cell-line, when measured using the MTT assay.
Rational Design of a DNA-Scaffolded High-Affinity Binder for Langerin
Bachem, Gunnar,Baukmann, Hannes,Dernedde, Jens,Fuchsberger, Felix,Kim, Dongyoon,Rademacher, Christoph,Seitz, Oliver,Silberreis, Kim,Wamhoff, Eike-Christian
supporting information, p. 21016 - 21022 (2020/09/21)
Binders of langerin could target vaccines to Langerhans cells for improved therapeutic effect. Since langerin has low affinity for monovalent glycan ligands, highly multivalent presentation has previously been key for targeting. Aiming to reduce the amoun
