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Issue 12, 2013
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Chemo-enzymatic synthesis and glycosidase inhibitory properties of DAB and LAB derivatives

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Abstract

A chemo-enzymatic strategy for the preparation of 2-aminomethyl derivatives of (2R,3R,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol (also called 1,4-dideoxy-1,4-imino-D-arabinitol, DAB) and its enantiomer LAB is presented. The synthesis is based on the enzymatic preparation of DAB and LAB followed by the chemical modification of their hydroxymethyl functionality to afford diverse 2-aminomethyl derivatives. This strategy leads to novel aromatic, aminoalcohol and 2-oxopiperazine DAB and LAB derivatives. The compounds were preliminarily explored as inhibitors of a panel of commercial glycosidases, rat intestinal disaccharidases and against Mycobacterium tuberculosis, the causative agent of tuberculosis. It was found that the inhibitory profile of the new products differed considerably from the parent DAB and LAB. Furthermore, some of them were active inhibiting the growth of M. tuberculosis.

Graphical abstract: Chemo-enzymatic synthesis and glycosidase inhibitory properties of DAB and LAB derivatives

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Publication details

The article was received on 03 Dec 2012, accepted on 24 Jan 2013 and first published on 24 Jan 2013


Article type: Paper
DOI: 10.1039/C3OB27343A
Org. Biomol. Chem., 2013,11, 2005-2021

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    Chemo-enzymatic synthesis and glycosidase inhibitory properties of DAB and LAB derivatives

    A. L. Concia, L. Gómez, J. Bujons, T. Parella, C. Vilaplana, P. J. Cardona, J. Joglar and P. Clapés, Org. Biomol. Chem., 2013, 11, 2005
    DOI: 10.1039/C3OB27343A

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