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Updated: Sep 28, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Molecular discrimination of N-protected amino acid esters by a self-assembled cylindrical capsule: spectroscopic and
Osamu Hayashida1, Lubomir Sebo, Julius Rebek
1The Skaggs Institute for Chemical Biology and The Department of Chemistry, The Scripps Research Institute, MB-26, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Abstract:
A self-assembled, cylindrical capsule was used to bind N-alpha-protected amino acid esters. The reversible encapsulation was studied using NMR spectroscopy in deuterated mesitylene solution and by computer-aided molecular modeling. BOC-L-alanine alkyl esters and BOC-beta-alanine alkyl esters were tested as guests, and the relative binding affinities were established by direct competition experiments. A good correlation was found between the experimental and calculated relative binding affinities in these two series. Guests that were slightly longer than the internal dimensions of the cavity were accommodated by adopting compacted conformations.
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