Chemo-enzymatic synthesis and glycosidase inhibitory properties of DAB and LAB derivatives.
Org Biomol Chem
; 11(12): 2005-21, 2013 Mar 28.
Article
in En
| MEDLINE
| ID: mdl-23381224
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.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Arabinose
/
Sugar Alcohols
/
Disaccharidases
/
Enzyme Inhibitors
/
Imino Furanoses
/
Glycoside Hydrolases
/
Anti-Bacterial Agents
/
Mycobacterium tuberculosis
Limits:
Animals
Language:
En
Journal:
Org Biomol Chem
Journal subject:
BIOQUIMICA
/
QUIMICA
Year:
2013
Document type:
Article
Affiliation country:
Spain