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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

Alexander Popkov ; Jiri Hanusek ; Jiri Cermak ; Vratislav Langer (Institutionen för kemi- och bioteknik, Oorganisk miljökemi) ; Robert Jirasko ; Michal Holcapek ; Milan Nadvornik
Journal of Radioanalytical and Nuclear Chemistry (0236-5731). Vol. 285 (2010), 3, p. 621-626.
[Artikel, refereegranskad vetenskaplig]

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.

Nyckelord: Amino acids, 6[18F]FDOPA, stereoselectivity, Nickel, PET, Schiff bases



Denna post skapades 2010-09-01. Senast ändrad 2015-07-01.
CPL Pubid: 125552

 

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Institutioner (Chalmers)

Institutionen för kemi- och bioteknik, Oorganisk miljökemi (2005-2014)

Ämnesområden

Biofysikalisk kemi
Bio-oorganisk kemi
Organisk syntes

Chalmers infrastruktur