Synthesis of enantiomerically pure α-[14C]methyl-L-tryptophan
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Add time:09/25/2019 Source:sciencedirect.com
A practical method for the preparation of large amounts of enantiomerically pure α-[14C]methyl-L-tryptophan using the enzymatic resolution of the corresponding D,L-methyl ester is reported. The radiolabelled α-methyl group was introduced using the α-methylation of the lithium enolate of the Schiff base of L-tryptophan methyl ester. Hydrolysis of the Schiff base with 1 N HCl provided the D,L-methyl ester of α-[14C]methyl tryptophan. Enantioselective enzymatic hydrolysis of the L-methyl ester by α-chymotrypsin gave the enantiomerically pure α-[14C]methyl-L-tryptophan. The overall yield of this preparation was 33%.
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