Accession Number : AD0444561

Title :   SYNTHESIS OF TRYPTOPHAN-CARBOXYL-14C1,

Corporate Author : NATIONAL RESEARCH COUNCIL OF CANADA SASKATOON (SASKATCHEWAN) PRAIRIE REGIONAL LAB

Personal Author(s) : Slater, G. P.

Report Date : 06 MAR 1964

Pagination or Media Count : 3

Abstract : Tryptophan labelled in the carboxyl group with carbon 14 was required for studies on the biosynthesis of a fungal metabolite, but was not commercially available. The synthesis was achieved from indole-3-aldehyde and hydantoin4-C14 using a modification of a procedure for the corresponding C13-labelled compound. In the modified method, indolylidenehydantoin was reduced by the action of Raney nickel alloy in dilute sodium hydroxide solution, instead of using Raney nickel catalyst in sodium hydroxide. The reduction product, indolylmethylhydantoin was not isolated, but its aqueous solution was hydrolyzed with barium hydroxide and the tryptophan isolated by ion-exchange chromatography. This procedure constitutes a facile synthesis of tryptophan and gives a better yield (73%) than a reported synthesis based on hydantoin. (Author)

Descriptors :   *LABELED SUBSTANCES, TRYPTOPHAN, SYNTHESIS(CHEMISTRY), CARBON, RADIOACTIVE ISOTOPES, HYDANTOINS, CATALYSTS, NICKEL ALLOYS, REDUCTION(CHEMISTRY), HYDROLYSIS, ION EXCHANGE, TRACER STUDIES.

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE