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Efficient Recognition of Chiral Carbamoyl‐α‐Hydroxyacids with a Cleft‐Type Receptor
Author(s) -
Martín Mercedes,
Raposo César,
Almaraz Marta,
Crego Mercedes,
Caballero Cruz,
Grande Manuel,
Morán Joaquín R.
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199623861
Subject(s) - chemistry , titration , enantiomer , stereochemistry , chirality (physics) , receptor , chromatography , combinatorial chemistry , organic chemistry , biochemistry , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
Simple chromatography using SiO 2 impregnated with ( S )‐4‐chlorophenyl‐carbamoyllactic acid (( S )‐ 2 ) can be used to separate the enantiomers of receptor 1 ( R f (( R )‐ 1 / R f (( S )‐ 1 ) = 0.8/0.1)). The very large association constant of the more stable complex [( R )‐ 1 ·( S )‐ 2 ] (5.7 × 10 5 M −1 ) was determined in a series of competitive NMR titrations with α‐amino acid derivatives, which form less stable complexes with 1 .
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