Synthesis of 5-Hydroxy-L-tryptophan Utilizing N-Acetyl-L-glutamic γ-Semialdehyde, an Intermediate in the Metabolism of L-Glutamic Acid to L-Ornithine

Abstract

N-Acetyl-L-glutamic γ-semialdehyde was enzymatically prepared in 51% yield from Na-acetyl-L-ornithine. By the reaction with 4-benzyloxy(or methoxy)-phenylhydrazine this aldehyde was converted into N-acetyl-5-benzyloxy(or methoxy)-L-tryptophan which is known to be transformed into 5-hydroxy-L-tryptophan, a biogenetic precursor of serotonin. By this work an amino acid of L-glutamic acid family was first chemically derived to that of L-trypto-phan series.