67546-20-7Relevant academic research and scientific papers
A Fluorescent Transport Assay Enables Studying AmpG Permeases Involved in Peptidoglycan Recycling and Antibiotic Resistance
Perley-Robertson, G. Evan,Yadav, Anuj K.,Winogrodzki, Judith L.,Stubbs, Keith A.,Mark, Brian L.,Vocadlo, David J.
, p. 2626 - 2635 (2016/10/07)
Inducible AmpC β-lactamases deactivate a broad-spectrum of β-lactam antibiotics and afford antibiotic resistance in many Gram-negative bacteria. The disturbance of peptidoglycan recycling caused by β-lactam antibiotics leads to accumulation of GlcNAc-1,6-anhydroMurNAc-peptides, which are transported by AmpG to the cytoplasm where they are processed into AmpC inducers. AmpG transporters are poorly understood; however, their loss restores susceptibility toward β-lactam antibiotics, highlighting AmpG as a potential target for resistance-attenuating therapeutics. We prepare a GlcNAc-1,6-anhydroMurNAc-fluorophore conjugate and, using live E. coli spheroplasts, quantitatively analyze its transport by AmpG and inhibition of this process by a competing substrate. Further, we use this transport assay to evaluate the function of two AmpG homologues from Pseudomonas aeruginosa and show that P. aeruginosa AmpG (Pa-AmpG) but not AmpP (Pa-AmpP) transports this probe substrate. We corroborate these results by AmpC induction assays with Pa-AmpG and Pa-AmpP. This fluorescent AmpG probe and spheroplast-based transport assay will enable improved understanding of PG recycling and of permeases from the major facilitator superfamily of transport proteins and may aid in identification of AmpG antagonists that combat AmpC-mediated resistance toward β-lactam antibiotics.
PROCESS FOR PREPARING HEPARINOIDS AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF
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, (2013/02/28)
Processes are disclosed for the synthesis of the Factor Xa anticoagulant fondaparinux and related compounds. Protected pentasaccharide intermediates and efficient and scalable processes for the industrial scale production of fondaparinux sodium by conversion of the protected pentasaccharide intermediates via a sequence of deprotection and sulfonation reactions are provided.
Synthesis of a heparan sulfate mimetic disaccharide with a conformationally locked residue from a common intermediate
Fairweather, Jon K.,Karoli, Tomislav,Liu, Ligong,Bytheway, Ian,Ferro, Vito
experimental part, p. 2394 - 2398 (2010/01/03)
A simple mimetic of a heparan sulfate disaccharide sequence that binds to the growth factors FGF-1 and FGF-2 was synthesized by coupling a 2-azido-2-deoxy-d-glucopyranosyl trichloroacetimidate donor with a 1,6-anhydro-2-azido-2-deoxy-β-d-glucopyranose acceptor. Both the donor and acceptor were obtained from a common intermediate readily obtained from d-glucal. Molecular docking calculations showed that the predicted locations of the disaccharide sulfo groups in the binding site of FGF-1 and FGF-2 are similar to the positions observed for co-crystallized heparin-derived oligosaccharides obtained from published crystal structures.
NOVEL ANTI-INFLAMMATORY PRO-DRUGS
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Page/Page column 18-19, (2009/01/24)
The present invention relates to compounds according to formula (I): wherein R is selected from the group consisting of anti-inflammatory agents and pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising compounds of formula (I) and the use of these pharmaceutical compositions for the treatment or prophylaxis of chronic inflammatory diseases, in particular those that are caused by chronically activated macrophages. The chronic inflammatory disease is in particular atherosclerosis, (rheumatoid) arthritis, an (auto)immune disease or sarcoidosis.
α:β Selectivity in the synthesis of 3-substituted, 4-methyl umbelliferone glycosides of N-acetyl glucosamine and chitobiose
Ganguli, Anjali R.S.,Coward, James K.
, p. 411 - 424 (2007/10/03)
The influence of phenolic acceptor nucleophilicity; for example, 3-substituted, 4-methylumbelliferones, and glycosyl donor electrophilicity; for example, 3- and 4-substituted N-acetylglucosamines, on glycosylation stereochemistry has been evaluated. In a systematic comparison, the stereochemical outcome as well as the reaction yield appeared to be influenced by the 3- and 4-substituents of the donor as well as the 3-substituent of the aryl acceptor. In the context of synthesizing a fluorogenic substrate for oligosaccharyltransferase, an α-glycoside was desired. Although most acceptor-donor pairs led to predominantly or exclusively the β-glycoside, reaction of the most activated (3,4-di-O-benzyl) donor and the least nucleophilic acceptor (3-Br), resulted in a 1:1 ratio of α,β arylglycosides.
Synthesis of polynitrogenated analogues of glucopyranoses from levoglucosan
Bailliez, Vincent,Olesker, Alain,Cleophax, Jeannine
, p. 1079 - 1085 (2007/10/03)
Polynitrogenated analogues of glucopyranoses were synthesised from levoglucosan. These compounds are useful intermediates for the synthesis of new aminoglycoside mimetics.
Investigation of the hydrogen bonding properties of a series of monosaccharides in aqueous media by 1H NMR and IR spectroscopy
Hawley, Joanne,Bampos, Nick,Aboitiz, Nuria,Jimenez-Barbero, Jesus,Lopez De La Paz, Manuela,Sanders, Jeremy K. M.,Carmona, Pedro,Vicent, Cristina
, p. 1925 - 1936 (2007/10/03)
A technique, based on 1H NMR and IR experiments, to characterise intramolecular hydrogen bonds in aqueous medium in a series of amino, amido and ammonium sugar derivatives has been established. Three groups of molecules, representing amides (4, 5 and 6), amines (7 and 8) and ammonium salts (chlorides 9 and 10, and phosphates 11 and 12), with different relative configurations of their functional groups, have been investigated to assess the effect of the nature and the stereochemistry of these groups on the hydrogen-bonding features of the sugar. The deduced features in water solution are compared to those obtained previously in nonpolar solvents. The phosphate salts of amines 7 and 8 (11 and 12) were also prepared, in order to evaluate the influence of the OH groups on the binding of the phosphate counterion, and the possibility of establishing cooperative hydrogen bonds involving the phosphate group. The data presented here indicate that the 1,3-cis-diaxial-type configuration in sugar diols and amino alcohols produces an intramolecular six-membered-ring hydrogen bond that survives in water and, moreover, offers the possibility to establish cooperative intermolecular hydrogen bonds. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
An Expeditious and Stereocontrolled Preparation of 2-Azido-2-deoxy-β-D-glucopyranose Derivatives from D-Glucal
Tailler, Denis,Jaquinet, Jean-Claude,Noirot, Anne-Marie,Beau, Jean-Marie
, p. 3163 - 3164 (2007/10/02)
1,6-Anhydro-2-azido-2-deoxy-β-D-glucopyranose has been prepared by a two-step procedure from D-glucal and transformed into precursors useful in the synthesis of oligosaccharides.
Facile Preparation of 3,4-Di-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose and Some Derivatives Thereof: Useful Precursors for Oligosaccharide Synthesis
Dasgupta, Falguni,Garegg, Per J.
, p. 626 - 628 (2007/10/02)
A facile, virtually one-pot synthesis of the title compound and also some of its derivatives is based on regioselective 2-substitutions of 1,6-anhydro-β-D-mannopyranose using stannylidene activation.The compounds thus prepared are useful precursors in the synthesis of glycoprotein-type oligosaccharides.
