Introduction of 4(S)-oxazolidineacetic acid, 2-oxo (D-Oxac) motif in a polypeptide chain: synthesis and conformational analysis.
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.
Luppi
Gianluigi
G
Dipartimento di Chimica G. Ciamician, Alma Mater Studiorum, Università di Bologna, Via Selmi, 2-40126 Bologna, Italy.
Villa
Marzia
M
Tomasini
Claudia
C
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
D000596:Amino Acids; D007555:Isoxazoles; D009842:Oligopeptides; D023303:Oxazolidinones