Solid-phase synthesis of beta-lactams via the Miller hydroxamate approach.
[figure: see text] beta-Lactams were prepared on solid phase starting from serine, threonine, or other beta-hydroxyacids derived from naturally occurring amino acids and a resin bound hydroxylamine. The ring closure was carried out under Mitsunobu conditions. The amino group present on the beta-lactam was used to assemble a short peptide. After a reductive cleavage with Sml2, beta-lactam-containing peptides were obtained.
Meloni
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Dipartimento di Chimica, Università degli Studi di Sassari, Via Vienna 2, I-07100 Sassari, Italy.
Taddei
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D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D006877:Hydroxamic Acids / Q000737:chemistry*; D006898:Hydroxylamines; D011137:Polystyrenes; D012694:Serine / Q000737:chemistry; D013912:Threonine / Q000737:chemistry; D047090:beta-Lactams / Q000138:chemical synthesis*
D000900:Anti-Bacterial Agents; D006877:Hydroxamic Acids; D006898:Hydroxylamines; D011137:Polystyrenes; D047090:beta-Lactams; D013912:Threonine; D012694:Serine