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Chiral Ligand Exchange Adsorbents for Amines and Underivatized Amino Acids: 'Bait-and-Switch' Molecular Imprinting

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
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/bk-1998-0703.ch007DOIArticle
https://pubs.acs.org/doi/abs/10.1021/bk-1998-0703.ch007PublisherArticle
ORCID:
AuthorORCID
Arnold, Frances H.0000-0002-4027-364X
Additional Information:© 1998 American Chemical Society. Published in print 7 May 1998. . This research is supported by the National Science Foundation (BES-9416915).
Funders:
Funding AgencyGrant Number
NSFBES-9416915
Series Name:ACS Symposium Series
Issue or Number:703
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:03 Oct 2019 19:34

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