Fmoc-protected, glycosylated asparagines potentially useful as reagents in the solid-phase synthesis of N-glycopeptides.
Carbohydr Res
; 235: 83-93, 1992 Nov 04.
Article
em En
| MEDLINE
| ID: mdl-1473114
ABSTRACT
1-Amino 1-deoxy derivatives of unprotected O-beta-D-galactopyranosyl-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyrano se, 2-acetamido-2-deoxy-D-galactose, D-galactose, lactose, D-fucose, D-mannose, and 2-deoxy-D-arabino-hexose were prepared and acylated with N-fluorenylmethoxycarbonylaspartic acid alpha-tert-butyl ester. The anomeric configuration of the N-glycosyl bond (including that of the mannose derivative) in each of the purified compounds was shown to be beta. The probable stability of the N-glycosyl and glycosidic bonds during the conditions of solid-phase peptide synthesis was investigated by treatment of the glycosylated asparagine derivatives with different concentrations of trifluoroacetic acid. Based on their stability, we found that Fmoc-Asn(sugar)-OH derivatives are excellent candidates for automated synthesis of biologically active glycopeptides.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Asparagina
/
Carboidratos
/
Glicopeptídeos
/
Dissacarídeos
Idioma:
En
Revista:
Carbohydr Res
Ano de publicação:
1992
Tipo de documento:
Article