title: NMR spectroscopic analysis of new spiro-piperidylrifamycins.
abstract: New spiro-piperidylrifamycin derivatives are presented. These compounds were synthesized from the reaction of 3-amino-4-iminorifamycin S and enantiomerically pure 4-piperidones, which generate diasteroisomeric rifabutin analogues with a new stereocentre at the spiranic carbon. The (1)H and (13)C NMR spectra of these new compounds, and also the configuration of the new stereogenic centres, were assigned using 2D NMR spectroscopic techniques. A preliminary study of the (1)H and (13)C NMR spectra of the starting compounds rifamycin S, 3-amino-4-iminorifamycin S and the related rifabutin was also carried out and as a result, their previously published (13)C NMR data were corrected.
authors.affiliation: Instituto Universitario de Química Organometálica Enrique Moles, Unidad Asociada al CSIC, Universidad de Oviedo, C/Julián Clavería 8, 33006 Oviedo, Spain. erubio@uniovi.es
authors.forename: Eduardo
authors.initials: E
authors.lastname: Rubio
authors.forename: Isabel
authors.initials: I
authors.lastname: Merino
authors.forename: Ana-Belén
authors.initials: AB
authors.lastname: García
authors.forename: María-Paz
authors.initials: MP
authors.lastname: Cabal
authors.forename: Cristina
authors.initials: C
authors.lastname: Ribas
authors.forename: Miguel
authors.initials: M
authors.lastname: Bayod-Jasanada
mesh_terms: D002247:Carbon Isotopes; D009682:Magnetic Resonance Spectroscopy / Q000379:methods* / Q000592:standards*; D008968:Molecular Conformation; D009615:Nocardia / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry; D011522:Protons; D012015:Reference Standards; D017828:Rifabutin / Q000737:chemistry; D012294:Rifamycins / Q000138:chemical synthesis / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C501220:3-amino-4-iminorifamycin S; D002247:Carbon Isotopes; D010880:Piperidines; D011522:Protons; D012294:Rifamycins; D013141:Spiro Compounds; D017828:Rifabutin; C032779:rifamycin S