Facile synthesis of stapled, structurally reinforced peptide helices via a photoinduced intramolecular 1,3-dipolar cycloaddition reaction.
We report the first use of a photoinduced 1,3-dipolar cycloaddition reaction in "stapling" peptide sidechains to reinforce a model peptide helical structure with moderate to excellent yields; the resulting pyrazoline "staplers" exhibit unique fluorescence useful in a cell permeability study.
Madden
Michael M
MM
Department of Chemistry, State University of New York at Buffalo, Buffalo, New York 14260, USA.
Rivera Vera
Claudia I
CI
Song
Wenjiao
W
Lin
Qing
Q
D000595:Amino Acid Sequence; D045744:Cell Line, Tumor; D005456:Fluorescent Dyes / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011720:Pyrazoles / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D014466:Ultraviolet Rays
D005456:Fluorescent Dyes; D010455:Peptides; D011720:Pyrazoles