Poly-L-proline type II peptide mimics based on the 3-azabicyclo[3.1.0]hexane system.
This paper describes conformational studies of proline-templated amino acids (PTAAs) based on the 3-azabicyclo[3.1.0]hexane system as well as conformational studies on short peptides composed of these PTAAs. NOE data, coupling constants, and molecular modeling are consistent with a flattened boat conformation for monomeric and oligomeric residues based on this bicyclic system. NMR studies on dimeric and trimeric oligomers are consistent with a populated poly-L-proline type II conformation in CDCl3 and D2O. Solution studies and molecular modeling predicts phi approximately -70 degrees, psi approximately 131 degrees, chi 1 approximately -57 degrees, and chi 2 approximately -158 degrees for oligomeric residues.
Mamai
A
A
Department of Chemistry, University of Vermont, Burlington, Vermont 05405, USA.
Zhang
R
R
Natarajan
A
A
Madalengoitia
J S
JS
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D019281:Dimerization; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D011392:Proline; D011487:Protein Conformation; D013329:Structure-Activity Relationship
D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D010455:Peptides; C011083:polyproline; D011392:Proline