Synthesis of gizzerosine, a toxic substance found in fish meal

Citation
C. Herrera et al., Synthesis of gizzerosine, a toxic substance found in fish meal, BOL SOC CH, 44(1), 1999, pp. 117-121
Citations number
9
Categorie Soggetti
Chemistry
Journal title
BOLETIN DE LA SOCIEDAD CHILENA DE QUIMICA
ISSN journal
03661644 → ACNP
Volume
44
Issue
1
Year of publication
1999
Pages
117 - 121
Database
ISI
SICI code
0366-1644(199903)44:1<117:SOGATS>2.0.ZU;2-H
Abstract
A simple methodology was used for the synthesis of racemic gizzerosine, who se S-enantiomer has been considered as the main responsible substance for p roducing the black vomit syndrome in birds. This work has been carried out using classical reactions of the traditional organic chemistry, based on th e Gabriel synthesis for the preparation of synthetic amino acids. With the use of easily available materials and reactants, this substance was obtaine d in reasonable yields and at a lower cost, than that reported previously b y others. The intermediaries were analyzed using physical and spectroscopic techniques. The synthetic gizzerosine, obtained in the present work, was c onfirmed as the expected product, corroborating the structure, by means of the proton nuclear magnetic resonance spectra. The results of the analyses were consistent with the data reported previously in literature, respect to the physical and chemical characterization of the final product of the des cribed synthesis pathway.