ASYMMETRIC SYNTHESIS OF α-AMINO ACIDS BY NONENZYMATIC TRANSAMINATION. RATIONALIZATION FOR THE STEREOCHEMICAL RESULTS
- 5 November 1982
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 11 (11) , 1769-1772
- https://doi.org/10.1246/cl.1982.1769
Abstract
Asymmetric induction in the nonenzymatic transamination from the chiral pyridoxamine analog (1) to the α-keto acids in the presence of a limited amount of zinc ion can be explained by the kinetically controlled stereoselective protonation to the carbanion formed in an octahedral Zn2+ chelate intermediate during the reaction.Keywords
This publication has 5 references indexed in Scilit:
- A new synthesis of (R)- and (S)-2-2H-amino acids, including (R)- and (S)-2-2H1-glycine via stereochemically inert Co(III) complexesTetrahedron, 1980
- Equilibria and solute structures in the aqueous systems pyridoxal-alanine-zinc(II) and -aluminum(III) as investigated by proton resonanceJournal of the American Chemical Society, 1969
- Pyridoxal Analogs. X. Zinc(II)-Chelate Catalysis of Transamination in Methanol SolutionJournal of the American Chemical Society, 1967
- Stereochemistry of The Manganese(II)-Pyridoxylidenevaline ChelateJournal of the American Chemical Society, 1963
- A General Mechanism for Vitamin B6-catalyzed Reactions1Journal of the American Chemical Society, 1954