Stereoselective synthesis of conformationally constrained omega-amino acid analogues from pyroglutamic acid.
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.
Bentz
Emilie L
EL
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK.
Goswami
Rajesh
R
Moloney
Mark G
MG
Westaway
Susan M
SM
D000596:Amino Acids / Q000737:chemistry*; D013058:Mass Spectrometry; D008968:Molecular Conformation; D011761:Pyrrolidonecarboxylic Acid / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D011761:Pyrrolidonecarboxylic Acid