title: Synthesis of strained cyclic peptides via an aza-Michael-acyl-transfer reaction cascade.
abstract: A new method is presented to prepare strained lactams. Esterification of the C-terminus of a dipeptide with β-nitrostyrene or quinoline-type auxiliaries is followed by lactam formation by an intramolecular aza-Michael-acyl-transfer reaction cascade. Ultimately, the cyclic tetrapeptide cyclo[Phe-Tyr-Ala-Gly] has been prepared.
authors: Van't Hoff Institute for Molecular Sciences, Science Park 904, 1098XH Amsterdam, The Netherlands.
authors: Jochem P A
authors: JP
authors: Rutters
authors: Yvette
authors: Y
authors: Verdonk
authors: Remko
authors: R
authors: de Vries
authors: Steen
authors: S
authors: Ingemann
authors: Henk
authors: H
authors: Hiemstra
authors: Vincent
authors: V
authors: Levacher
authors: Jan H
authors: JH
authors: van Maarseveen
mesh_terms: D000595:Amino Acid Sequence; D003500:Cyclization; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry; D013343:Styrenes / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D007769:Lactams; D010456:Peptides, Cyclic; D011804:Quinolines; D013343:Styrenes; C011955:beta-nitrostyrene