<Emphasis Type="Italic">N</Emphasis>-Bromoacetyl-β-<Emphasis Type="SmallCaps">D</Emphasis>-glycopyranosylamines in the synthesis of glycoconjugates of nitrogen-containing physiologically active compounds |
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Authors: | L M Likhosherstov O S Novikova A O Zheltova V N Shibaev |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | A series of nitrogen-containing physiologically active compounds underwent smooth N-monoalkylation with N-bromoacetyl-β-glycopyranosylamines derived from N-acetyl-D-glucosamine and lactose. This reaction was demonstrated to be promising for the introduction of carbohydrate residues into
heterocyclic compounds, viz., pyridine, imidazole, pyrimidinetrione, carboline, and piperazine derivatives, and into an amino acid, 5-hydroxy-L-tryptophan, which is unstable in alkaline media.
Dedicated to Academician N. K. Kochetkov on the occasion of his 90th birthday.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1256–1259, May, 2005. |
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Keywords: | N-bromoacetyl-β -glycopyranosylamines N-monoalkylation glycoconjugates |
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