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https://hdl.handle.net/2440/32209
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Type: | Journal article |
Title: | A small-scale synthesis and enantiomeric resolution of (RS)-[1-C-¹⁴]-2-phenylpropionic acid and biosynthesis of its diastereomeric acyl glucuronides |
Other Titles: | A small-scale synthesis and enantiomeric resolution of (RS)-[1-C-(14)]-2-phenylpropionic acid and biosynthesis of its diastereomeric acyl glucuronides |
Author: | Shackleford, David M. Hayball, Peter John Reynolds, Geoffrey D. Hamon, David P. G. Evans, Allan Mark Milne, Robert W. Nation, Roger L. |
Citation: | Journal of Labelled Compounds & Radiopharmaceuticals, 2001; 44(3):225-234 |
Publisher: | John Wiley & Sons |
Issue Date: | 2001 |
ISSN: | 0362-4803 |
School/Discipline: | School of Chemistry and Physics |
Statement of Responsibility: | David M. Shackleford, Peter J. Hayball, Geoffrey D. Reynolds, David P.G. Hamon, Allan M. Evans, Robert W. Milne, Roger L. Nation |
Abstract: | The 3 step synthesis for (RS)-[1-14C]-2-phenylpropionic acid having overall yield of 30% is reported. The enantiomers were separated to an optical purity of 95 % (90 % ee) by semi-preparative chiral HPLC using an α1-acid glycoprotein-based column (which has not previously been reported for this separation). Subsequently, the diastereomeric acyl glucuronides of (R)- and (S)-[1-14C]-2-phenylpropionic acid were biosynthesised using a recirculating-mode isolated perfused rat liver preparation. The procedure for purification of the glucuronides by semi-preparative HPLC was optimised to ensure the biosynthetic products did not undergo degradation via acyl migration or hydrolysis. |
Keywords: | (RS)-[1-14C]-2-phenylpropionic acid ; acyl glucuronides ; phase transfer catalyst ; chiral HPLC |
Rights: | Copyright © 2001 John Wiley & Sons, Ltd. |
DOI: | 10.1002/jlcr.450 |
Appears in Collections: | Chemistry and Physics publications |
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