Synthesis of Two Epimers of Pseudopaline. Issue 26 (2nd July 2020)

• Record Type: Journal Article
• Authors: Cullia, Gregorio; Fanelli, Roberto; Voulhoux, Romé; Arnoux, Pascal; Cavelier, Florine
• Is Part Of: European journal of organic chemistry. Issue 26(2020)
• Page Start: 3975
• Page End: 3980
• Publication Date: 2020-07-02
• Subjects: Natural products -- Amino acids -- Opines -- Pseudopaline -- Total synthesis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000278
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Opines are a known group of compounds characterized by an elevated polarity. Recently, two new members of this class, staphylopine and pseudopaline, have been identified in Staphylococcus aureus and Pseudomonas aeruginosa, respectively. These molecules are metal chelators that contribute to the growth of bacteria in particularly metal‐poor environment. Different evidences suggest that these molecules might have an important role in the development of pulmonary infections in humans. Considering the impact of P. aeruginosa infections in cystic fibrosis patients (prevalence up to 70 %), pseudopaline has risen interest as potential source of new therapeutic intervention. We present herein a straightforward synthetic approach for the synthesis of the two epimers of pseudopaline. Starting from a chiral building block, we attribute the absolute configuration to the two obtained diasteroisomers. Abstract : Pseudopaline is an opine metal chelator recently identified in Pseudomonas aeruginosa. This metallophore plays an important role in bacterial development during infections, providing a route for the acquirement of essential micronutrients (Zn 2+ and Mn 2+ ) in metal scarce environments. Herein, a straightforward synthetic approach for the synthesis of two epimers of pseudopaline and the attribution of their absolute configurations is presented.