title: Stereoselective synthesis of conformationally constrained omega-amino acid analogues from pyroglutamic acid.
abstract: Bicyclic lactams derived from pyroglutamic acid provide a useful scaffold for synthesis of conformationally restricted analogues of lysine, ornithine and glutamine, as well as an Ala-Ala dipeptide analogue. Amino alcohol and carboxylic acid derivatives are accessible from a common intermediate. In this strategy, the bicyclic lactam system not only controls, but also facilitates the determination of the stereochemistry of the synthetic intermediates.
authors: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK.
authors: Emilie L
authors: EL
authors: Bentz
authors: Rajesh
authors: R
authors: Goswami
authors: Mark G
authors: MG
authors: Moloney
authors: Susan M
authors: SM
authors: Westaway
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D013058:Mass Spectrometry; D008968:Molecular Conformation; D011761:Pyrrolidonecarboxylic Acid / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D011761:Pyrrolidonecarboxylic Acid