Semi-synthesis of a 3-O-sulfated red seaweed galactan-derived disaccharide alditol.
Carbohydr Res
; 341(10): 1753-7, 2006 Jul 24.
Article
em En
| MEDLINE
| ID: mdl-16516874
ABSTRACT
Beta-D-Galp3-SO3-(1-->4)-3,6-anhydro-L-GalOH (agarobiitol 3(2)-sulfate, 4) was semi-synthetically prepared as follows production of agarobiitol (1) from agarose by partial reductive hydrolysis, protection of the primary hydroxyl groups of 1 with trityl groups to produce the 1(1),6(2)-di-O-tritylated derivative (2), regioselective dibutylstannylene-mediated sulfation of 2 to give the 3(2)-O-sulfated-1(1),6(2)-di-O-tritylated compound (3), and detritylation of compound 3 to give the final product (4). This semi-synthetic route allowed the preparation of a red seaweed galactan-derived disaccharide alditol with sulfate group located at C-3 of the galactopyranosidic ring. Because red seaweed galactans are glycosidically linked at C-3 of the beta-D-Galp unit, a sulfated derivative with this structure could not be obtained by partial reductive hydrolysis of sulfated red seaweed galactans.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Dissacarídeos
/
Galactanos
Idioma:
En
Ano de publicação:
2006
Tipo de documento:
Article