Development of metallocomplex amino acids synthons for the asymmetric preparation of alpha-amino acids by stereoselective introduction of a side chain. Evaluation of the model asymmetric preparation of alanine and beta-C-13 monolabelled alpha-aminoisobutyric acid

作者：Popkov Alexander^*; Hanusek Jiri; Cermak Jiri; Langer Vratislav; Jirasko Robert; Holcapek Michal; Nadvornik Milan

来源：Journal of Radioanalytical and Nuclear Chemistry, 2010, 285(3): 621-626.

DOI：10.1007/s10967-010-0578-5

• Amino acids
• 6-[F-18]FDOPA
• Stereoselectivity
• Nickel
• PET
• Schiff bases

In this communication the evaluation of eleven new metallocomplex alanine synthons bearing C-2-symmetric benzyl groups with electron-donating and electron-withdrawing substituents is described. alpha-Methylated glycine synthons (alanine complexes) were evaluated alongside alanine synthons in order to obtain a deeper understanding of the relationship between their structures and stereochemistry of monoalkylated products and to choose several candidates for their further tests for stereospecific preparation of 6-[F-18]FDOPA. Glycine-derived analogues of the complexes 3-5 are the best candidates for the development of a 6-[F-18]FDOPA preparation procedure. In the model epimerisation reaction they demonstrated the best performance, much better compared to the previously described compound 2. Complexes 3, 5 and 8 are the best in asymmetric preparation of beta-C-13 monolabelled alpha-aminoisobutyric acid. They have to be tested in the preparation of alpha-methyl amino acids like 6-[F-18]-alpha-methylDOPA and 2-[F-18]-alpha-methyltyrosine.

• 出版日期2010-9