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Issue 21, 2011
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Bicyclic amino acid-carbohydrate-conjugates as conformationally restricted hydroxyethylamine (HEA) transition-state isosteres

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Abstract

This communication describes a general synthetic route to bicyclic amino acid-carbohydrate-conjugates, which would be useful as conformationally restricted hydroxyethylamine (HEA) transition-state isosteres. The synthesis was achieved in 12 steps starting from D-glucose. The striking features of this system are the bicyclic rigid core displaying an α-amino acid side chain and hydroxyethylamine moiety – both of which would be potentially important for receptor interactions, leading to various biomedical responses, as described in the literature. Crystal structure investigation suggested extensive intermolecular hydrogen-bonding interactions in this system, involving the backbone amide and hydroxyl groups.

Graphical abstract: Bicyclic amino acid-carbohydrate-conjugates as conformationally restricted hydroxyethylamine (HEA) transition-state isosteres

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Publication details

The article was received on 20 Jul 2011, accepted on 31 Aug 2011 and first published on 01 Sep 2011


Article type: Communication
DOI: 10.1039/C1OB06215H
Org. Biomol. Chem., 2011,9, 7300-7302

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    Bicyclic amino acid-carbohydrate-conjugates as conformationally restricted hydroxyethylamine (HEA) transition-state isosteres

    S. S. Kale, S. T. Chavan, S. G. Sabharwal, V. G. Puranik and G. J. Sanjayan, Org. Biomol. Chem., 2011, 9, 7300
    DOI: 10.1039/C1OB06215H

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