Diverted Total Synthesis of Promysalin Analogs Demonstrates That an Iron-Binding Motif Is Responsible for Its Narrow-Spectrum Antibacterial Activity.
J Am Chem Soc
; 138(18): 5833-6, 2016 05 11.
Article
de En
| MEDLINE
| ID: mdl-27096543
ABSTRACT
Promysalin is a species-specific Pseudomonad metabolite with unique bioactivity. To better understand the mode of action of this natural product, we synthesized 16 analogs utilizing diverted total synthesis (DTS). Our analog studies revealed that the bioactivity of promysalin is sensitive to changes within its hydrogen bond network whereby alteration has drastic biological consequences. The DTS library not only yielded three analogs that retained potency but also provided insights that resulted in the identification of a previously unknown ability of promysalin to bind iron. These findings coupled with previous observations hint at a complex multifaceted role of the natural product within the rhizosphere.
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Sujet principal:
Pyrrolidines
/
Salicylamides
/
Fer
/
Antibactériens
Type d'étude:
Prognostic_studies
Langue:
En
Journal:
J Am Chem Soc
Année:
2016
Type de document:
Article
Pays d'affiliation:
États-Unis d'Amérique