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A Small‐Molecule Guanidinium Receptor: The Arginine Cork
Author(s) -
Bell Thomas W.,
Khasanov Alisher B.,
Drew Michael G. B.,
Filikov Anton,
James Thomas L.
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990903)38:17<2543::aid-anie2543>3.0.co;2-9
Subject(s) - dipeptide , hydrogen bond , arginine , chemistry , molecule , receptor , crystal structure , guanidine , crystallography , stereochemistry , polar , amino acid , biochemistry , organic chemistry , physics , astronomy
A highly preorganized, artificial receptor for guanidinium cations binds arginine with high affinity in polar solvents, even in water! The X‐ray crystal structure of its bis( N ‐ethylguanidinium) complex shows the formation of hydrogen bonds between the receptor and the guest (see picture). This observation explains the strength of the complex formed with the dipeptide diarginine ( K d =50 μ M in H 2 O).