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Fmoc-protected, glycosylated asparagines potentially useful as reagents in the solid-phase synthesis of N-glycopeptides

✍ Scribed by Laszlo Urge; Laszlo Otvos Jr.; Emma Lang; Krzysztof Wroblewski; Ilona Laczko; Miklos Hollosi

Publisher: Elsevier Science
Year: 1992
Tongue: English
Weight: 768 KB
Volume: 235
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(92)80080-k

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✦ Synopsis

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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