Development of metallocomplex amino acids synthons for the asymmetric preparation of α-amino acids by stereoselective introduction of a side chain. Evaluation of the model asymmetric preparation of alanine and β-13C monolabelled α-aminoisobutyric acid
Artikel i vetenskaplig tidskrift, 2010

In this communication the evaluation of eleven new metallocomplex alanine synthons bearing C2-symmetric benzyl groups with electron-donating and electron-withdrawing substituents is described. α-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-[18F]FDOPA. Glycine-derived analogues of the complexes 3–5 are the best candidates for the development of a 6-[18F]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 β-13C monolabelled α-aminoisobutyric acid. They have to be tested in the preparation of α-methyl amino acids like 6-[18F]-α-methylDOPA and 2-[18F]-α-methyltyrosine.

Nickel

stereoselectivity

PET

Schiff bases

6[<sup>18</sup>F]FDOPA

Amino acids

Författare

Alexander Popkov

Jiri Hanusek

University of Pardubice

Jiri Cermak

Vuzkumnu ustav organickuch syntez a.s

Vratislav Langer

Chalmers, Kemi- och bioteknik, Oorganisk miljökemi

Robert Jirasko

University of Pardubice

Michal Holcapek

University of Pardubice

Milan Nadvornik

University of Pardubice

Journal of Radioanalytical and Nuclear Chemistry

0236-5731 (ISSN) 1588-2780 (eISSN)

Vol. 285 621-626

Ämneskategorier

Oorganisk kemi

Fysikalisk kemi

Organisk kemi

DOI

10.1007/s10967-010-0578-5