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Bending Rigid Molecular Rods: Formation of Oligoproline Macrocycles
Author(s) -
Scully Conor C. G.,
Rai Vishal,
Poda Gennadiy,
Zaretsky Serge,
Burns Darcy C.,
Houliston R. Scott,
Lou Tiantong,
Yudin Andrei K.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203266
Subject(s) - image stitching , polyproline helix , aziridine , bent molecular geometry , bending , circular dichroism , chemistry , crystallography , stereochemistry , peptide , materials science , computer science , biochemistry , organic chemistry , artificial intelligence , composite material , ring (chemistry)
Bent but not broken : Cyclic oligoprolines are accessed in a reaction that effectively bends rigid oligoproline peptides (see scheme; TBDMS= tert ‐butyldimethylsilyl). The stitching is accomplished during macrocyclization enabled by aziridine aldehydes and isocyanides. Molecular modeling studies suggest that electrostatic attraction between the termini of the linear peptide is pivotal for macrocyclization. The macrocycles were studied by circular dichroism with a polyproline II structure being observed in larger macrocycles.