Arnold, Frances H. and Striegler, Susanne and Sundaresan, Vidyasankar (1998) Chiral Ligand Exchange Adsorbents for Amines and Underivatized Amino Acids: 'Bait-and-Switch' Molecular Imprinting. In: Molecular and Ionic Recognition with Imprinted Polymers. ACS Symposium Series. No.703. American Chemical Society , Washington, DC, pp. 109-118. ISBN 9780841235748. https://resolver.caltech.edu/CaltechAUTHORS:20180406-091535284
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Abstract
Ligand-exchange adsorbents for the chiral separation of underivatized α-amino acids and amine analogs have been prepared by molecular imprinting with a polymerizable copper complex and the amino acid as template. Because the complexation equilibria in these mixed-ligand systems involve numerous species, it is extremely important to characterize the template:monomer assemblies prior to polymerization. Isothermal titration calorimetry and classical species distribution diagrams have been used to determine the conditions under which the amino acids (phenylalanine) form strong 1:1 mixed-ligand complexes with the copper-iminodiacetate (CuIDA) functional monomer. In contrast, a diamine template ethylenediamine does not form 1:1 complexes with CuIDA; the diamine instead competes with IDA for the metal ion, and a stronger chelating group is required. Adsorbents prepared using enantiomers of phenylalanine as template show enantioselectivity for phenylalanine and tyrosine as well as for a chiral amine analog of phenylalanine, α-methylphenethylamine. The use of the amino acid as the template in this 'bait-and-switch' imprinting approach allows creation of chirally selective binding sites suitable for separations of chiral amines.
Item Type: | Book Section | |||||||||
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Additional Information: | © 1998 American Chemical Society. Published in print 7 May 1998. . This research is supported by the National Science Foundation (BES-9416915). | |||||||||
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Series Name: | ACS Symposium Series | |||||||||
Issue or Number: | 703 | |||||||||
DOI: | 10.1021/bk-1998-0703.ch007 | |||||||||
Record Number: | CaltechAUTHORS:20180406-091535284 | |||||||||
Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20180406-091535284 | |||||||||
Official Citation: | Chiral Ligand Exchange Adsorbents for Amines and Underivatized Amino Acids: 'Bait-and-Switch' Molecular Imprinting Frances H. Arnold, Susanne Striegler, and Vidyasankar Sundaresan Molecular and Ionic Recognition with Imprinted Polymers. May 7, 1998, 109-118 DOI:10.1021/bk-1998-0703.ch007 | |||||||||
Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
ID Code: | 85676 | |||||||||
Collection: | CaltechAUTHORS | |||||||||
Deposited By: | Ruth Sustaita | |||||||||
Deposited On: | 06 Apr 2018 17:41 | |||||||||
Last Modified: | 15 Nov 2021 20:31 |
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