Title

Synthesis And Biological Evaluation Of New Acinetoferrin Homologues For Use As Iron Transport Probes In Mycobacteria

Abstract

Four new acinetoferrin homologues were synthesized using a modular synthetic approach. Two linear and two cyclic imide derivatives were generated and evaluated for growth stimulating behavior in Mycobacterium avium subsp paratuberculosis. The yield for the tandem coupling of a functionalized aminohydroxamic acid motif (2 equiv) to a tert-butyl citrate derivative was significantly improved using DCC and N-hydroxysuccinimide. 1H NMR spectroscopy (CD3OD) provided a convenient method for monitoring the final imidization step in TFA using the doublet patterns between 2.5 and 3.06 ppm. New protocols demonstrated that only a 20% growth enhancement was observed with M. avium subsp. paratuberculosis using the imide of acinetoferrin. Last, a siderophore from Streptomyces pilosus, deferrioxamine B, was shown to cross-feed M. avium subsp. paratuberculosis with the same efficiency as the more costly, native chelator, mycobactin J.

Publication Date

9-23-2004

Publication Title

Journal of Medicinal Chemistry

Volume

47

Issue

20

Number of Pages

4933-4940

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1021/jm049805y

Socpus ID

4544380267 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/4544380267

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