Issue 21, 2006
From the journal:

Organic & Biomolecular Chemistry

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

Kevin M. Bucholtz,cd   Peter C. Gareiss,bd   Stephen G. Tajcbd  and  Benjamin L. Miller*abd  

* Corresponding authors

a Department of Dermatology, University of Rochester, Rochester, New York, USA
E-mail: Benjamin_Miller@futurehealth.rochester.edu
Fax: +1 (1)585 273 1346
Tel: +1 (1)585 275 9805

b Department of Biochemistry and Biophysics, University of Rochester, Rochester, New York, USA

c Department of Chemistry, University of Rochester, Rochester, New York, USA

d Center for Future Health, University of Rochester, Rochester, New York, USA

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/B610727C
Article type
Paper
Submitted
25 Jul 2006
Accepted
13 Sep 2006
First published
29 Sep 2006

Org. Biomol. Chem., 2006,4, 3973-3979

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

K. M. Bucholtz, P. C. Gareiss, S. G. Tajc and B. L. Miller, Org. Biomol. Chem., 2006, 4, 3973 DOI: 10.1039/B610727C

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