10.1016/S0008-6215(00)85248-9
A study detailing the synthesis of a glycotripeptide and a glycosomatostatin, both containing the 3-O-(2-acetamido-2-deoxy-D-glucopyranosyl)-L-serine residue. The research was conducted by a team from the Salk Institute for Biological Studies and the University of California, San Diego. The process involved solid-phase synthesis to create the sequences Gly-[P-D-GlcpNAc-(1→3)-Ser]-Ala-OH and /I-D-GlcpNAc-(1→3)-Ser-13-somatostatin. The synthesized glycopeptides were found to be homogeneous upon examination through thin-layer chromatography (t.l.c.) and liquid chromatography (l.c.), and they exhibited the correct amino acid composition and 2-amino-2-deoxy-D-glucose content. The structure of one of the glycopeptides was confirmed by mass spectrometry and nuclear magnetic resonance (n.m.r.) spectroscopy. The study was supported by grants from the National Institute of Arthritis, Metabolism, and Digestive Diseases, the National Heart Institute, and the William Randolph Hearst Foundation, among others.
10.1016/0008-6215(83)88254-8
This research aims to develop a convenient and practical method for synthesizing complex saccharides that are part of glycoconjugates. The study focuses on synthesizing a key intermediate compound for the production of a specific carbohydrate structure found in blood-group substances. The researchers used various chemicals, including benzyl alcohol, mercuric cyanide, hexamethyl-disilazane, chlorotrimethylsilane, acetic anhydride, and 2,2-dimethoxypropane, among others, to achieve the desired synthesis. The process involved multiple steps of acetylation, deacetylation, silylation, and isopropylidenation. The final product was obtained in good yields and its structure was confirmed through NMR spectroscopy. The study concludes that the synthesized intermediate could be a suitable precursor for the further synthesis of more complex oligosaccharides, potentially useful in the study of glycosidases, glycosyltransferases, and as synthetic antigens.