International Journal of Peptide and Protein Reseach 1987-01-01

Synthesis of 3-(3-pyridyl)- and 3-(3-benzo[b]thienyl)-D-alanine.

P N Rao, J E Burdett, J W Cessac, C M DiNunno, D M Peterson, H K Kim

Index: Int. J. Pept. Protein Res. 29(1) , 118-25, (1987)

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Abstract

The DL-arylamino acid ethyl ester derivatives of beta-(3-pyridyl)-DL-alanine, and beta-(3-benzo[b]thienyl)-DL-alanine were synthesized by diethyl acetamidomalonate condensation with the respective arylmethyl halides followed by partial hydrolysis to the monoethyl ester and decarboxylation. Each derivative was enzymatically resolved to a separable mixture of the corresponding N-acetyl-L-amino acid and the unchanged D amino acid derivative. Acidic hydrolysis of the latter gave the corresponding D-amino acid, the optical purity of which was established by HPLC analysis of the 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate (GITC) derivative. The free D amino acids were converted to D-BOC derivatives by reaction with di-tert-butyldicarbonate in tert-butyl alcohol, water and sodium hydroxide.