Premium
Synthesis of Two Epimers of Pseudopaline
Author(s) -
Cullia Gregorio,
Fanelli Roberto,
Voulhoux Romé,
Arnoux Pascal,
Cavelier Florine
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000278
Subject(s) - pseudomonas aeruginosa , epimer , chemistry , staphylococcus aureus , molecule , bacteria , combinatorial chemistry , stereochemistry , small molecule , microbiology and biotechnology , computational biology , biochemistry , biology , organic chemistry , genetics
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.