title: Efficient total syntheses and biological activities of two teixobactin analogues.
abstract: The discovery of the new antibiotic teixobactin has been timely in the race for unearthing novel antibiotics wherein the emergence of drug resistant bacteria poses a serious threat worldwide. Herein, we present the total syntheses and biological activities of two teixobactin analogues. This approach is simple, efficient and has several advantages: it uses commercially available building blocks (except AllocHN-d-Thr-OH), has a single purification step and a good recovery (22%). By using this approach we have synthesised two teixobactin analogues and established that the d-amino acids are critical for the antimicrobial activity of these analogues. With continuing high expectations from teixobactin, this work can be regarded as a stepping stone towards an in depth study of teixobactin, its analogues and the quest for synthesising similar molecules.
authors.affiliation: School of Pharmacy, JBL Building, University of Lincoln, Beevor St. Lincoln LN67DL, UK. isingh@lincoln.ac.uk.
authors.forename: Anish
authors.initials: A
authors.lastname: Parmar
authors.affiliation: School of Pharmacy, JBL Building, University of Lincoln, Beevor St. Lincoln LN67DL, UK. isingh@lincoln.ac.uk and Organic and Biomimetic Chemistry Research Group, Department of Organic Chemistry, Ghent University, Krijgslaan 281 (S4), B-9000 Ghent, Belgium.
authors.forename: Abhishek
authors.initials: A
authors.lastname: Iyer
authors.affiliation: School of Life Sciences, JBL Building, University of Lincoln, Beevor St. Lincoln LN67DL, UK. etaylor@lincoln.ac.uk.
authors.forename: Charlotte S
authors.initials: CS
authors.lastname: Vincent
authors.affiliation: Organic and Biomimetic Chemistry Research Group, Department of Organic Chemistry, Ghent University, Krijgslaan 281 (S4), B-9000 Ghent, Belgium.
authors.forename: Dorien
authors.initials: D
authors.lastname: Van Lysebetten
authors.affiliation: School of Chemistry, JBL Building, University of Lincoln, Beevor St. Lincoln LN67DL, UK.
authors.forename: Stephen H
authors.initials: SH
authors.lastname: Prior
authors.affiliation: Organic and Biomimetic Chemistry Research Group, Department of Organic Chemistry, Ghent University, Krijgslaan 281 (S4), B-9000 Ghent, Belgium.
authors.forename: Annemieke
authors.initials: A
authors.lastname: Madder
authors.affiliation: School of Life Sciences, JBL Building, University of Lincoln, Beevor St. Lincoln LN67DL, UK. etaylor@lincoln.ac.uk.
authors.forename: Edward J
authors.initials: EJ
authors.lastname: Taylor
authors.affiliation: School of Pharmacy, JBL Building, University of Lincoln, Beevor St. Lincoln LN67DL, UK. isingh@lincoln.ac.uk.
authors.forename: Ishwar
authors.initials: I
authors.lastname: Singh
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000494:pharmacology*; D004926:Escherichia coli / Q000187:drug effects*; D004927:Escherichia coli Infections / Q000188:drug therapy; D006801:Humans; D008826:Microbial Sensitivity Tests; D013203:Staphylococcal Infections / Q000188:drug therapy; D013211:Staphylococcus aureus / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D047630:Depsipeptides; C000594838:teixobactin