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Issue 23, 2007
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A versatile strategy for the synthesis of N-linked glycoamino acids from glycals

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Abstract

A versatile route for the synthesis of N-linked glycoamino acids from readily available glycals is reported. A variety of glycals possessing different carbohydrate templates (mono-, di- and trisaccharide glycals) were shown to undergo a novel iodine catalyzed stereoselective diamination reaction with chloramine-T. Taking advantage of the difference in the reactivity between the anomeric and C2 sulfonamido groups of these diamines 7, 13, 15, 17 and 19, they could be protected differentially at the C2 and anomeric nitrogen atoms. Thus, chemoselective acetylation of these diamines installed the C2 acetamido group, an essential functionality that plays a crucial role in inducing a β-turn in N-linked glycoproteins. Subsequent protection of the anomeric nitrogens of 20a,b,e as their Alloc (allyloxycarbonyl) derivatives followed by SmI2 mediated facile didetosylation afforded 24a–c. Deprotection of the Alloc group of 24a and 24c and coupling of the liberated free amine with a variety of protected amino acids provided N-linked glycoamino acids 25 and 27 in high yields. An illustrative synthesis of an N-linked glycopeptide 29 is also reported.

Graphical abstract: A versatile strategy for the synthesis of N-linked glycoamino acids from glycals

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Publication details

The article was received on 20 Aug 2007, accepted on 02 Oct 2007 and first published on 19 Oct 2007


Article type: Paper
DOI: 10.1039/B712841J
Citation: Org. Biomol. Chem., 2007,5, 3847-3858
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    A versatile strategy for the synthesis of N-linked glycoamino acids from glycals

    V. Kumar and N. G. Ramesh, Org. Biomol. Chem., 2007, 5, 3847
    DOI: 10.1039/B712841J

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