A novel and efficient asymmetric synthesis of carbon-14 labeled (S,S)-2,7-di-boc-diamino[1,8-14C2]suberic acid
| Autor: | J. R. Heys, A. J. Villani, Arthur Shu, D. Saunders |
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| Rok vydání: | 2002 |
| Předmět: |
chemistry.chemical_classification
Chiral auxiliary Nitrile Organic Chemistry Strecker amino acid synthesis Enantioselective synthesis Diastereomer Biochemistry Analytical Chemistry chemistry.chemical_compound Dicarboxylic acid chemistry Drug Discovery Organic chemistry Radiology Nuclear Medicine and imaging Enantiomer Suberic acid Spectroscopy |
| Zdroj: | Journal of Labelled Compounds and Radiopharmaceuticals. 45:49-57 |
| ISSN: | 1099-1344 0362-4803 |
| DOI: | 10.1002/jlcr.534 |
| Popis: | Five hundred mCi of Potassium [14C]cyanide at a specific activity of 51 mCi/mmol was used to diastereoselectively introduce the carbon-14 label into 1,6-hexanedial via a thermodynamically controlled asymmetric Strecker reaction using (R)-(-)-2-phenylglycinol as the chiral auxiliary. The expected and predominant (R,S/S,R) diastereomer (2) was separated by preparative normal phase HPLC. The chiral auxiliary was removed by oxidation with lead tetraacetate and the resulting benzylimino nitrile exhaustively hydrolyzed in hydrochloric acid to give (S,S)-2,7-diamino[1,8-14C2]suberic acid (6). Subsequent acylation with di-tert-butyldicarbonate gave the title compound (1) with a radiochemical purity of 95.5%, a specific activity of 113 mCi/mmol, and an enantiomeric purity of 95.5% e.e. To our knowledge this is the first report of the asymmetric Strecker methodology being applied to the synthesis of a carbon-14 labeled amino acid. Copyright © 2002 John Wiley & Sons, Ltd. |
| Databáze: | OpenAIRE |
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