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 described ter-cycloalkane based lipid A-binding compounds.
Bucholtz
Kevin M
KM
Department of Chemistry, University of Rochester, Rochester, New York, USA.
Gareiss
Peter C
PC
Tajc
Stephen G
SG
Miller
Benjamin L
BL
D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D004926:Escherichia coli / Q000737:chemistry / Q000166:cytology; D006863:Hydrogen-Ion Concentration; D008024:Ligands; D008050:Lipid A / Q000737:chemistry* / Q000378:metabolism*; D013056:Spectrophotometry, Ultraviolet; D013816:Thermodynamics
D003503:Cyclobutanes; D008024:Ligands; D008050:Lipid A