Synthesis and 12-helical secondary structure of beta-peptides containing (2R,3R)-aminoproline.
[structure: see text] (2R,3R)-Aminoproline, a pyrrolidine-based beta-amino acid, was synthesized and incorporated into hexa-beta-peptide 4. This residue confers water solubility when the ring nitrogen is protonated and allows for 12-helix formation in aqueous solution. Circular dichroism spectra display the 12-helical signature, and 12-helical structure was confirmed by 2D NMR analysis.
Porter
Emilie A
EA
Department of Chemistry, University of Wisconsin, Madison 53706, USA.
Wang
Xifang
X
Schmitt
Margaret A
MA
Gellman
Samuel H
SH
D002942:Circular Dichroism; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000378:metabolism*; D017433:Protein Structure, Secondary; D012995:Solubility; D012996:Solutions
D010455:Peptides; D012996:Solutions; C467925:aminoproline; D011392:Proline