Chemoselective synthesis of sialic acid 1,7-lactones.
J Org Chem
; 75(16): 5542-8, 2010 Aug 20.
Article
em En
| MEDLINE
| ID: mdl-20704429
ABSTRACT
The chemoselective synthesis of the 1,7-lactones of N-acetylneuraminic acid, N-glycolylneuraminic acid, and 3-deoxy-d-glycero-d-galacto-nononic acid is accomplished in two steps:
a simple treatment of the corresponding free sialic acid with benzyloxycarbonyl chloride and a successive hydrogenolysis of the formed 2-benzyloxycarbonyl 1,7-lactone. The instability of the 1,7-lactones to protic solvents has been also evidenced together with the rationalization of the mechanism of their formation under acylation conditions. The results permit to dispose of authentic 1,7-sialolactones to be used as reference standards and of a procedure useful for the preparation of their isotopologues to be used as inner standards in improved analytical procedures for the gas liquid chromatography-mass spectrometry (GLC-MS) analysis of 1,7-sialolactones in biological media.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Ácidos Siálicos
/
Lactonas
Tipo de estudo:
Guideline
Idioma:
En
Ano de publicação:
2010
Tipo de documento:
Article