Publication year: 2011
Source: Journal of Chromatography A, Available online 9 November 2011

Carlo Bertucci, Marco Pistolozzi, Daniele Tedesco, Riccardo Zanasi, Renzo Ruzziconi, ...

Enantioselective high performance liquid chromatography (HPLC) coupled with a detection system based on the simultaneous measurement of UV absorption and electronic circular dichroism (ECD) allows a complete stereochemical characterization of chiral compounds, once the relationship between sign of the chiroptical properties and absolute configuration is determined. In the present communication, the development of enantioselective HPLC methods for the resolution of a series of fluorinated 2-phenanthrenylpropionic acids (1-6) is reported. Different chiral stationary phases (CSPs) were tested: ChiralcelOJ, ChiralcelOD, ChiralpakAD, (S,S)-Whelk-O1, Chirobiotic™ T andα1-acid glycoprotein (AGP).The results allow the application of the methods to a reliable determination of the enantiomeric excess for all the examined compounds; the highest enantioselectivity values were obtained with the Hibar[(S,S)-Whelk-O1] column for some of the examined compounds. In the case ofrac-2-(6-fluorophenanthren-1-yl)propionic acid (1), the relationship between circular dichroism and absolute configuration of the enantiomeric fractions was determined by ECD analysis and time-dependent density functional theory (TD-DFT) calculations.The experimental ECD spectrum of the second-eluted fraction of 1 on the Hibar[(S,S)-Whelk-O1] column was found to be in excellent agreement with the theoretical ECD spectrum of (S)-1; therefore, the absolute configuration of the first- and second-eluted enantiomers on the (S,S)-Whelk-O1 CSP was assessed as (R) and (S), respectively, and the elution orders of the enantiomeric forms of 1 were determined on all the different CSPs.

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[Article No. 5IAW4] Mallory, Ellen; White, Charles; Morris, Thomas; Kiernan, Nancy Ellen
Reading the Farm is a 2- to 3-day professional development program that brings together agricultural service providers from a range of agencies, with various expertise and levels of experience, to explore whole-farm systems and sustainability through in-depth study of two case-study farms. Over 90% of past participants reported that the program has helped them be more effective service providers. In this article, we describe the program and draw on our experiences in three states to provide recommendations for future implementation of the program.