Preparation, properties and absolute configuration of (-)-allantoin

Autor: G. D. Vogels, E. J. 's-Gravenmade, Corry van Pelt
Rok vydání: 2010
Předmět:
Zdroj: Recueil des Travaux Chimiques des Pays-Bas. 88:929-939
ISSN: 0165-0513
DOI: 10.1002/recl.19690880806
Popis: A procedure is given for the preparation and isolation of (-)-allantoin (5-ureidohydantoin). A grown culture of Pseudomonas aeruginosa was incubated with (±)-allantoin at pH 6. (+)-Allantoin was degraded by the bacteria and (-)-allantoin was removed from the medium with the aid of activated carbon. Several properties of (-)-allantoin were determined: solubility and molar rotation in various solvents, infrared spectrum, decomposition point and dependence of the molar rotation on pH. The properties were compared with those of (±)-allantoin, R- and S-hydantoin-5-acetic acid. From circular dichroism measurements of (-)-allantoin, S-hydantoin-5-acetic acid and R-carbamoylalanine it was concluded that (-)-allantoin is R-allantoin.
Databáze: OpenAIRE