The construction and stereoselective synthesis of new derivatives of 2-aminopropionic acids

Organic and Bioorganic Chemistry

Abstract

The nature of the interaction of (S)-2-aminopropionic acid and its 2-methyl substituted derivatives containing benzoyl or 4-benzoylphenyl substituent in position 3 and (S)-2-(3- benzoylphenyl)propionic acid with the voltage gated bacterial sodium channel 3rw0 (Arcobacter butzleri) was studied by DOCKING analysis. Binding energies (DG0) with sodium channel were determined for all acids and it was shown that the derivatives of (S)-2-methyl-2-amino- and (S)-2- aminopropionic acids bound most effectively to 4-benzoylphenyl substituent in position 3. Then, a method for the asymmetric synthesis of three new derivatives of aminopropionic acid - (S)-2-amino-3-(4-benzoylphenyl)propionic acid (ee=95.09%, t = 25 min), (S)-2-amino-3-(benzoyl) propionic acid (ee = 94. 16 %, t = 27 min) and (S)-2-methyl-2-amino-3-(4-benzoylphenyl)propionic acid (ee = 96. 24%, t = 70 min) was developed under base catalysis through C-alkylation of NiII - complexes of Schiff bases of glycine and alanine with chiral auxiliary (S)-2-N-[N’- (benzylprolyl)aminbenzophenone by benzoylbromomethane or 4-benzoylphenylbromomethane