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

Alda Lisa Concia, Livia Gómez, Jordi Bujons, Teodor Parella, Cristina Vilaplana, Pere Joan Cardona, Jesús Joglar, Pere Clapés

Research output: Contribution to journalArticleResearchpeer-review

18 Citations (Scopus)

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. © 2013 The Royal Society of Chemistry.
Original languageEnglish
Pages (from-to)2005-2021
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number12
DOIs
Publication statusPublished - 28 Mar 2013

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