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Synthesis and Analysis of Bacterial Folate Metabolism Intermediates and Antifolates.

Authors :
Dawadi S
Kordus SL
Baughn AD
Aldrich CC
Source :
Organic letters [Org Lett] 2017 Oct 06; Vol. 19 (19), pp. 5220-5223. Date of Electronic Publication: 2017 Sep 19.
Publication Year :
2017

Abstract

The mechanism of action of para-aminosalicylic acid (PAS), a drug used to treat drug-resistant tuberculosis (TB), has been confirmed through the first synthesis and biochemical characterization of its active metabolite 7. The synthesis features the coupling of N <superscript>2</superscript> -acetyl-6-formylpterin obtained from the degradation of folic acid and appropriately functionalized arylamines to form Schiff bases. The sequential chemoselective reduction of the imine and pterin ring led to the formation of dihydrofolate analogue 7 and two other dihydropteroate species.

Details

Language :
English
ISSN :
1523-7052
Volume :
19
Issue :
19
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
28926267
Full Text :
https://doi.org/10.1021/acs.orglett.7b02487