A very versatile chemioenzymatic synthesis of stereospecifically labelled amino acids first developed in our laboratory has been altered and improved so that only chemical steps are involved. Unlike the original synthesis, monodeuteriated compounds can be obtained so that isotope effects can be clearly identified. The synthesis has been used to prepare (2R,3R)-[3-2H1]-p-chloroalanine, (2R,3S)-[3-2H1]-p-chloroalanine, (2S,3R)[ 3}Hd-p-chloroalanine and (2S,3S)-[3-2Hd-p-chloroalanine. The first two compounds were incubated with D-amino acid aminotransferase, and the second two compounds were incubated with L-aspartate aminotransferase. The stereochemical outcome of these reactions indicated retention of stereochemistry in the processes, casting light on similarities between the evolutionary families of PLP-dependent enzymes. A synthesis of stereospecifically labelled (2S)-propargylglycine was attempted. The key intermediates (2S,3R)-[3-2H1]-N-2-nitrobenzenesulfonylaziridine-2-carboxylate and (2S,3S)-[3-2H d-N -2-nitrobenzenesulfonylaziridine-2-carboxylate were synthesised and regiospecific ring opening of the intermediates was achieved. Time did not permit full deprotection of these products
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:405712 |
| Date | January 2004 |
| Creators | Lowpetch, Kreingkrai |
| Publisher | University of Sussex |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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