Synthesis and evaluation of the first cis-cyclobutane-containing receptor for lipid A

The first example of a designed receptor containing a cis-1,3-disubstituted cyclobutane ring has been synthesized. This molecule binds diphosphoryl lipid A (a conserved portion of the Gram-(-) bacterial cell membrane, and the causative agent of septic shock) with an affinity comparable to previously...

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Veröffentlicht in:	Organic & biomolecular chemistry 2006-01, Vol.4 (21), p.3973-3979
Hauptverfasser:	Bucholtz, Kevin M, Gareiss, Peter C, Tajc, Stephen G, Miller, Benjamin L
Format:	Artikel
Sprache:	eng
Schlagworte:	Cyclobutanes - chemical synthesis Cyclobutanes - chemistry Cyclobutanes - metabolism Escherichia coli - chemistry Escherichia coli - cytology Hydrogen-Ion Concentration Ligands Lipid A - chemistry Lipid A - metabolism Spectrophotometry, Ultraviolet Thermodynamics
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Beschreibung
Zusammenfassung:	The first example of a designed receptor containing a cis-1,3-disubstituted cyclobutane ring has been synthesized. This molecule binds diphosphoryl lipid A (a conserved portion of the Gram-(-) bacterial cell membrane, and the causative agent of septic shock) with an affinity comparable to previously described ter-cycloalkane based lipid A-binding compounds.
ISSN:	1477-0520 1477-0539
DOI:	10.1039/b610727c