Monitoring of optical isomers of some conformationally constrained amino acids with tetrahydroisoquinoline or tetraline ring structures. Part II

Add time:07/12/2019    Source:sciencedirect.com

Conformationally constrained amino acids were synthesized in chiral or racemic forms: d- amd l-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic), the erythro-d,l-4-methyl analogue, d- and l-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, d- and l-7-hydroxy-6,8-diiodo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, d,l-2-aminotetraline-2-carboxylic acid, d,l-6-hydroxy-2-aminotetraline-2-carboxylic acid and d,l-6-methoxy-2-aminotetraline-2-carboxylic acid. The optical isomers were characterized and identified by applying precolumn derivatization with chiral reagents (1-fluoro-2,4-dinitrophenyl-5-l-alanine amide and 2,3,4,5-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate) and enzymatic digestion with l-amino acid oxidase, carboxypeptidase A and α-chymotrypsin. The HPLC conditions (pH, eluent composition and different buffers) were varied to obtain optimum separations.

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