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Enantioselective Hosts for Neutral Derivatives of Amino Acids
Author(s) -
Clark Still W.,
Kilburn Jeremy D.,
Sanderson Philip E.J.,
Liu Ruiping,
Wiley Michael R.,
Hollinger Frank P.,
Hawley Ronald C.,
Nakajima Makoto,
Bernardi Anna,
Hong JongIn,
Namgoong Sung Keon
Publication year - 1992
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.199200006
Subject(s) - chemistry , hydrogen bond , titration , enantioselective synthesis , acceptor , molecular model , amino acid , stereochemistry , receptor , molecule , organic chemistry , catalysis , biochemistry , physics , condensed matter physics
A series of macropolycyclic receptors for hydrogen bond donor/acceptor guests were prepared and studied. Molecular modeling and X‐ray crystallography provided structural information, while NMR titration studies allowed determination of free energies of association. Some of die receptors prepared showed enantioselectivity as high as 3 kcal/mol in binding derivatives of simple amino acids in organic solvents. These studies show that conformational homogeneity is one of the most important characteristics of a selective host and that molecular modeling can play an important role in the design of such substances.