Synthese des Ophidins
- 1 January 1956
- journal article
- research article
- Published by Walter de Gruyter GmbH in Hoppe-Seyler´s Zeitschrift Für Physiologische Chemie
- Vol. 304 (Jahresband) , 77-81
- https://doi.org/10.1515/bchm2.1956.304.1-2.77
Abstract
Ophidlne was isolated by Imamura from snake muscle, and identified by Kendo as 2-methyl-N alpha-(beta-alanyl)-l-histidine; it is thus an isomer of anserine, and a homologue of carno-sine. This structure has now been confirmed by synthesis. 2-Methyl-4(5)- hydroxymethyl- imidazole was synthesized according to Lewis and Totter from fructose, ammonia and acetaldehyde. This was converted via the chlormethyl derivative to 2-methyl-histidine. This synthesis is fully described. 2 -Methyl-l-histidine was obtained by resolution of acetyl-2-methyl-dl-histidine by means of acylase I according to Greenstein. 2-Methyl-l-hlstidine was then coupled with phthaloyl-beta-alanyl-chloride, and the product decomposed with hydrazine to yield 2-methyl-N alpha-(beta-alanyl)-l-histidine. The picrolonate of this compound showed no M.P. depression with the picrolonate of ophldine as isolated from snake muscle.Keywords
This publication has 1 reference indexed in Scilit:
- Preparation of the optical isomers of arginine, histidine and S-benzylcysteine by asymmetric enzymatic hydrolysis of their acetyl derivativesArchives of Biochemistry and Biophysics, 1952