title: Introduction of 4(S)-oxazolidineacetic acid, 2-oxo (D-Oxac) motif in a polypeptide chain: synthesis and conformational analysis.
abstract: A four step synthesis of 4(S)-oxazolidineacetic acid, 2-oxo benzyl ester (D-Oxac-OBn) from L-Asp-OH in 45% overall yield is reported. The formation of by-products is completely avoided, by microwave irradiation and by the use of caesium carbonate as base. Moreover the synthesis and IR and 1H NMR conformational analysis of the tetramers Boc-L-Val-D-Oxac-L-Ala-OBn and Boc-L-Val-D-Oxac-Aib-L-Ala-OBn in solution is reported.
authors.affiliation: Dipartimento di Chimica G. Ciamician, Alma Mater Studiorum, Università di Bologna, Via Selmi, 2-40126 Bologna, Italy.
authors.forename: Gianluigi
authors.initials: G
authors.lastname: Luppi
authors.forename: Marzia
authors.initials: M
authors.lastname: Villa
authors.forename: Claudia
authors.initials: C
authors.lastname: Tomasini
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D023303:Oxazolidinones / Q000737:chemistry*; D017433:Protein Structure, Secondary; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D007555:Isoxazoles; D009842:Oligopeptides; D023303:Oxazolidinones