The synthesis of (5R)- and (5S)-[5-3H]-L-ornithine
β Scribed by Ronald J. Parry; Shyhchen Ju; Bill J. Baker
- Book ID
- 102901145
- Publisher
- John Wiley and Sons
- Year
- 1991
- Tongue
- French
- Weight
- 507 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0022-2135
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β¦ Synopsis
A practical synthesis of (5R)and (5S)-[5-3H]-L-ornithine is described. The key steps in the synthesis are the reduction of vonnyl-3H]J-hexenal with S-or R-Alpine Borane to (1R)and (1s)-[ 1-3H]J-hexen-l-ol and the use of the Evans electrophilic azidation of c h i d h i d e enolates to introduce the a-amino group of ornithine. The stereochemistry expected for the Alpine Borane reduction was v d i e d by NMR analysis of the camphanate ester derived from reduction of vomyf-2H]-S-hexenal with R-Alpine Borane.
π SIMILAR VOLUMES
No-carrier-added L-[5-11C]ornithine was synthesized in 25-40% radiochemical yield in a synthesis time of 50 min (EOB) and a specific ac vity >2.1 Ci/umol by the displacement reaction of potassium ['fC]cyanide with the functionally protected y- bromohomoserine followed by selective reduction of the [
## Abstract The title compound was obtained by preferential crystallisation of (2RS,5R)β[5β^2^H]proline. The labelled racemic amino acid was synthesized in five steps from (5R)β[5β^2^H]β2βpyrrolidone, which was prepared by cyclisation of (4R)β[4β^2^H] GABA. The stereospecific label was introduced i