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4-Amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid (β-TOAC), the first spin-labelled, cyclic, chiral β-amino acid resolved in an enantiomerically pure state |
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| Authors: | Karen Wright Marco CrismaClaudio Toniolo Roland TörökAntal Péter Michel WakselmanJean-Paul Mazaleyrat |
| Institution: | a SIRCOB, UMR CNRS 8086, Bât. Lavoisier, University of Versailles, F-78000 Versailles, France b Institute of Biomolecular Chemistry, CNR, Department of Organic Chemistry, University of Padova, I-35131 Padova, Italy c Department of Inorganic and Analytical Chemistry, University of Szeged, PO Box 440, H-6701 Szeged, Hungary |
| Abstract: | Amination of 3-carboxymethyl-1-oxyl-2,2,6,6-tetramethyl-4-piperidone with (R)-α-methylbenzylamine, NaBH3CN reduction of the resulting enamine and removal of the chiral auxiliary from the separated diastereoisomers, led to enantiomerically pure (3S,4S) and (3R,4R) methyl 4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylates. |
| Keywords: | chiral nitroxides modified β-amino acids spin-labelled amino acids |
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