- An improved procedure for the synthesis of N-bromoacetyl-β- glycopyranosylamines, derivatives of mono- and disaccharides
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An improved procedure for the synthesis of N-bromoacetyl-β- glycopyranosylamines from the corresponding β-glycosylamines was developed. The procedure is applicable to a wide range of derivatives of monosaccharides (hexoses, 2-acetamido-2-deoxyhexoses, hexuronamides, and 6-deoxyhexoses) and some disaccharides. For the derivatives of pentoses and 2-deoxyhexoses, the use of the corresponding β-glycosylammonium carbamates was found to be more convenient. N-Bromoacetyl-β-glycopyranosylamines derived from D-mannose, L-rhamnose, D-glucuronamide, 2-deoxy-D-arabino-hexose, 2-deoxy-D-lyxo-hexose, and melibiose were obtained for the first time.
- Likhosherstov,Novikova,Zheltova,Shibaev
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p. 709 - 713
(2007/10/03)
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- Synthesis of N4-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine analogues. Complete NMR assignments of chloroacetamide, bromoacetamide and glycinamide analogues
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N4-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine is the principle linkage in the structure of N-linked glycoproteins. Complete assignments of the 1H and 13C NMR spectra for three analogues of the naturally-occurring N-glycosylic structure were made for N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)chloroacetamide, N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)bromoacetamide and N1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)glycinamide. The methylene groups adjacent to the N-glycosylic bond are AB spin systems. Copyright
- Malik, Jayshri J.,Risley, John M.
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- Chemoselective elaboration of O-linked glycopeptide mimetics by alkylation of 3-thioGalNAc
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A critical branch point in mucin-type oligosaccharides is the β1 → 3 glycosidic linkage to the core α-N-acetylgalactosamine (GalNAc) residue. We report here a strategy for the synthesis of O-linked glycopeptide analogues that replaces this linkage with a
- Marcaurelle,Bertozzi
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p. 1587 - 1595
(2007/10/03)
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- Synthesis and biological activity of some 1-N-substituted 2-acetamido-2-deoxy-beta-D-glycopyranosylamine derivatives and related analogs.
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Several 1-N-substituted derivative [haloacetyl-, glycyl-, (dimethyl)amino-acetyl-, azidoacetyl-, trifluoroacetyl-, and trifluoromethylsulfonyl-] of 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranosylamine (1) were synthesized as potential metabolic inhibitors of cellular-membrane glycoconjugates. Several fully acetylated derivatives were found to inhibit growth of mouse mammary adenocarcinoma TA3, leukemia L1210, or leukemia P-288 cells at 1-0.01 mM concentration in vitro. Some of these derivatives were less active after O-deacetylation. Analogs of 1 in which NH2-1 was replaced by OH- or OAc-1 were also active on the same cell systems. The growth-inhibitory activity was correlated with inhibition of the incorporation of 2-amino-deoxy-D-glucose and L-leucine into a macromolecular fraction.
- Paul,Bernacki,Korytnyk
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