Design and characterization of a calixarene inclusion compound for calibration of long-range carbon-fluorine distance measurements by solid-state NMR.
An inexpensive, easily synthesized calixarene:fluorotoluene host:guest inclusion complex has been designed for optimization and calibration of solid-state NMR measurements of carbon-fluorine distances using Rotational Echo DOuble Resonance (REDOR). Complexation of the fluorotoluene with the calixarene host separates the molecules such that simple two-spin behavior is observed for one site with a 4.08 Å carbon-fluorine distance. Fluorotoluene dynamics within the calixarene matrix cause motional averaging of the dipolar couplings, which makes it possible to easily optimize REDOR experiments and test their accuracy for relatively long distance measurements (>6.6 Å). This provides a new tool for accurate REDOR measurements of long carbon-fluorine distances, which have important applications in the characterization of fluorine-containing drugs, proteins, and polymers.
Fowler
Daniel J
DJ
Department of Chemistry, University of Massachusetts Amherst. 710 N. Pleasant St., Amherst, MA 01003, USA.
Khalifah
Peter G
PG
Thompson
Lynmarie K
LK
D002138:Calibration; D047250:Calixarenes / Q000138:chemical synthesis / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008958:Models, Molecular
D007202:Indicators and Reagents; D047250:Calixarenes; D005461:Fluorine; D002244:Carbon
J Magn Reson. 2003 Jun;162(2):479-86
12810033
Biochemistry. 1994 Jul 26;33(29):8651-61
8038154
J Magn Reson. 2008 Mar;191(1):7-15
18155936
Talanta. 2009 Mar 15;77(5):1814-20
19159804
J Magn Reson. 2000 Dec;147(2):296-330
11097821
J Magn Reson. 2002 Jan;154(1):28-45
11820824
Angew Chem Int Ed Engl. 2003 Dec 15;42(48):5973-7
14679546
J Am Chem Soc. 2007 Jan 17;129(2):361-70
17212416
J Magn Reson. 2003 Dec;165(2):230-6
14643704
Biophys J. 1998 Nov;75(5):2574-6
9788953
J Magn Reson. 2004 Jun;168(2):358-65
15140448
J Magn Reson. 1997 Aug;127(2):147-54
9281478
Biochemistry. 2010 Feb 23;49(7):1425-34
20088541
J Am Chem Soc. 2009 Aug 19;131(32):11558-70
19627092
Chem Commun (Camb). 2004 Jun 21;(12):1360-1
15179464