Synthesis of Neu5Ac- and Neu5Gc-α-(2→6′)-lactosamine 3-aminopropyl glycosides

Sherman, Andrei A.; Yudina, O. N.; Shashkov, Alexander S.; Men’shov, V. M.; Nifant'ev, Nikolay E.

doi:10.1016/s0008-6215(01)00002-7

Cited by 57 publications

(21 citation statements)

References 16 publications

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“…Spectra of derivatives 4, 8, 10, and 24 coincided with those described before [8,12,13]. Chemical shift of H-3 eq (Neu5Ac, Neu5Gc and 9-deoxy-9-NAc-Neu5Ac residues) was 2.6-2.7 ppm for α-anomer and 2.2-2.4 ppm for β-anomer [3].…”

Section: Introductionsupporting

confidence: 80%

Koenigs-Knorr Glycosylation with Neuraminic Acid Derivatives

Pazynina

Nasonov

Belyanchikov

et al. 2010

International Journal of Carbohydrate Chemistry

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Earlier we reported a convenient and efficient method of preparing α2-6 sialooligosaccharides in conditions of Koenigs-Knorr reaction. The use of Ag 2 CO 3 allowed carrying out α2-6 sialylation of galacto-4,6-diol of mono-and disaccharides with chloride of acetylated N-acetylneuraminic acid methyl ester as glycosyl donor. In this study we applied this approach to other derivatives of neuraminic acid, namely, Neu5Gc, 9-deoxy-9-NAc-Neu5Ac, Neu5Acα2-8Neu5Ac, and Neu5Acα2-8Neu5Acα2-8Neu5Ac as glycosyl donors; eight compounds were synthesized: Neu5Gcα-O(CH 2 ) 3 NH 2 (8), Neu5Gcα2-6Galβ1-4GlcNAcβ-O(CH 2 ) 3 NH 2 (10), 9-deoxy-9-NAc-Neu5Ac-O(CH 2 ) 3 NH 2 (15), 9-deoxy-9-NAc-Neu5Acα2-6Galβ1-4GlcNAcβ-O(CH 2 ) 3 NH 2 (17), Neu5Acα2-8Neu5Acα-O(CH 2 ) 3 NH 2 (23) Neu5Acα2-8Neu5Acα-OCH 3 (24), Neu5Acα2-8Neu5Acα-OCH 2 (p-C 6 H 4 )NHCOCH 2 NH 2 (25), and Neu5Acα2-8Neu5Acα2-8Neu5Acα-O(CH 2 ) 3 NH 2 (32). These sialosides were used for characterization of siglecs and other carbohydrate-binding proteins.

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Section: Introductionsupporting

confidence: 80%

Koenigs-Knorr Glycosylation with Neuraminic Acid Derivatives

Pazynina

Nasonov

Belyanchikov

et al. 2010

International Journal of Carbohydrate Chemistry

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“…Finally, the disaccharide 4 was used to prepare a useful N-differenciated building block donor, 16, by oxazoline formation and installation of a tert-butyloxycarbonyl (Boc) group, in an overall yield of 70 %. This N,N-Boc,Ac motif has already been used at the C5 position of sialyl donors, [32] and proved to be stable under glycosylation conditions (NIS/cat·TfOH).…”

mentioning

confidence: 99%

From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG‐chitotriomycin

et al. 2014

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The direct and chemoselective N-transacylation of peracetylated chitooligosaccharides (COSs), readily obtained from chitin, to give per-N-trifluoroacetyl derivatives offers an attractive route to size-defined COSs and derived glycoconjugates. It involves the use of various acceptor building blocks and trifluoromethyl oxazoline dimer donors prepared with efficiency and highly reactive in 1,2-trans glycosylation reactions. This method was applied to the preparation of the important symbiotic glycolipids which are highly active on plants and to the TMG-chitotriomycin, a potent and specific inhibitor of insect, fungal, and bacterial N-acetylglucosaminidases.

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“…Therefore, our synthesis commenced with preparing trisaccharide donor 5 using monosaccharide intermediates 7, 74 8, 75 and 9 71,76 (Scheme 1). They were assembled in a linear sequence given rise to trisaccharide 13 (Scheme 2).…”

Section: Chemical Synthesis Of Aminooxy-globo H Antigenmentioning

confidence: 99%