title: Structural characterization of an enantiomerically pure amino acid imidazolide and direct formation of the beta-lactam nucleus from an alpha-amino acid.
abstract: Decomposition of a diazo beta-ketoamide derived from N-trityl serine imidazolide and N-protected acetanilides provides, instead of the expected 3-acyloxindole product, an enantiomerically pure (EP) beta-lactam. The amino acid stereocenter is incorporated, the second chiral center is induced, and trityl protection of the beta-lactam ring is realized for the first time. The desired 3-acyloxindole is obtained from oxindole and Tr-Ser(OBn)-imidazole, the X-ray of which provides the first structural determination of an EP amino acid imidazolide.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA.
authors.forename: Brian S
authors.initials: BS
authors.lastname: Gerstenberger
authors.forename: Jinzhen
authors.initials: J
authors.lastname: Lin
authors.forename: Yvette S
authors.initials: YS
authors.lastname: Mimieux
authors.forename: Lauren E
authors.initials: LE
authors.lastname: Brown
authors.forename: Allen G
authors.initials: AG
authors.lastname: Oliver
authors.forename: Joseph P
authors.initials: JP
authors.lastname: Konopelski
mesh_terms: D000083:Acetanilides / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D012694:Serine / Q000737:chemistry; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis*
chemical_list: D000083:Acetanilides; D000596:Amino Acids; D007093:Imidazoles; D007211:Indoles; D047090:beta-Lactams; D012694:Serine