title: Synthesis, FT-IR, ¹H, ¹³CNMR, ESI MS and PM5 studies of a new Mannich base of polyether antibiotic - Lasalocid acid and its complexes with Li⁺, Na⁺ and K⁺ cations.
abstract: The polyether antibiotic Lasalocid acid has been converted to its Mannich base derivative by a chemoselective one-pot reaction with formaldehyde and morpholine through the decarboxylation process. Spectroscopic studies of the structure of this new derivative have shown that in this ortho-phenol Mannich base the O-H⋯N intarmolecular hydrogen bond is present. The compound forms complexes with Li(+), Na(+) and K(+) cations of exclusively 1:1 stoichiometry. The structures of these complexes have been studied and visualized by semi-empirical calculation based on results of spectrometric and spectroscopic investigation. It is demonstrated that in contrast to Lasalocid acid the novel Mannich type derivative forms preferential complexes with Li(+) cation.
authors.affiliation: Faculty of Chemistry, Adam Mickiewicz University, ul. Umultowska 89b, 61-614 Poznań, Poland. adhucz@amu.edu.pl
authors.forename: Adam
authors.initials: A
authors.lastname: Huczyński
authors.forename: Jacek
authors.initials: J
authors.lastname: Rutkowski
authors.forename: Bogumil
authors.initials: B
authors.lastname: Brzezinski
authors.forename: Franz
authors.initials: F
authors.lastname: Bartl
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002247:Carbon Isotopes; D002412:Cations / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D006860:Hydrogen Bonding; D007832:Lasalocid / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008352:Mannich Bases / Q000138:chemical synthesis / Q000737:chemistry*; D008956:Models, Chemical; D011188:Potassium / Q000737:chemistry; D011522:Protons; D012964:Sodium / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000900:Anti-Bacterial Agents; D002247:Carbon Isotopes; D002412:Cations; D004987:Ethers; D008352:Mannich Bases; D011522:Protons; D008094:Lithium; D012964:Sodium; D011188:Potassium; D007832:Lasalocid