1. Oligomers of a 5-carboxy-methanopyrrolidine β-amino acid. A search for order
- Author
-
Charles DeBrosse, Guoliang Lin, Matthew Sender, Ryan Centafont, Grant R. Krow, Nian Liu, Matthew D. Shoulders, Patrick J. Carroll, Philip E. Sonnet, Ronald T. Raines, and Charles W. Ross
- Subjects
chemistry.chemical_classification ,Models, Molecular ,Pyrrolidines ,Molecular Structure ,Stereochemistry ,Hydrogen bond ,In silico ,Organic Chemistry ,Biochemistry ,Pyrrolidine ,Article ,Amino acid ,Hexane ,chemistry.chemical_compound ,chemistry ,Tetramer ,Molecule ,Physical and Theoretical Chemistry ,Amino Acids ,Protein secondary structure - Abstract
CD spectra for homooligomers (n = 4, 6, 8) of (1S,4R,5R)-5-syn-carboxy-2-azabicyclo[2.1.1]hexane (MPCA), a methano-bridged pyrrolidine β-carboxylic acid, suggest an ordered secondary structure. Even in the absence of internal hydrogen bonding, solution NMR, X-ray, and in silico analyses of the tetramer are indicative of conformations with trans-amides and C(5)-amide-carbonyls oriented toward the C(4) bridgehead. This highly constrained β-amino acid could prove useful in the ongoing development of well-defined foldamers.
- Published
- 2010