Helicity induction on a poly(phenylacetylene) derivative bearing aza‐18‐crown‐6 ether pendants in water

A stereoregular poly(phenylacetylene) bearing the bulky aza-18-crown-6 ether as the pendant (poly-1) formed a predominantly one-handed helical conformation upon complexation with various chiral compounds, such as amino acids, peptides, aminosugars, amines, and amino alcohols in water. The complexes exhibited an induced circular dichroism (ICD) in the UV–visible region of the polymer main chain. Therefore, poly-1 can be used as a novel probe for determining the chirality of chiral compounds in water. The assay of 19 common free L-amino acids gave the same ICD sign at 0 °C except for L-phenylalanine. The effects of pH, temperature, guest concentration, and organic solvent content on the ICD during the complexation of poly-1 with chiral compounds were also investigated. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 41: 1004–1013, 2003

[1]  E. Yashima,et al.  Detection and amplification of a small enantiomeric imbalance in alpha-amino acids by a helical poly(phenylacetylene) with crown ether pendants. , 2003, Journal of the American Chemical Society.

[2]  Bradley D. Smith,et al.  Membrane disruption ability of facially amphiphilic helical peptides. , 2002, Chemical communications.

[3]  Hiroshi Tsukube,et al.  Lanthanide complexes in molecular recognition and chirality sensing of biological substrates. , 2002, Chemical reviews.

[4]  E. Yashima.  Chiral and Chirality Discrimination on Helical Polyacetylenes , 2002 .

[5]  E. Yashima,et al.  Switching of a macromolecular helicity for visual distinction of molecular recognition events. , 2001, Journal of the American Chemical Society.

[6]  E. Yashima,et al.  A helical polyelectrolyte induced by specific interactions with biomolecules in water. , 2001, Journal of the American Chemical Society.

[7]  E. Yashima,et al.  Stereospecific Polymerization of Propiolic Acid with Rhodium Complexes in the Presence of Bases and Helix Induction on the Polymer in Water , 2001 .

[8]  E. Yashima,et al.  Molecular Recognition of Nucleosides and Nucleotides Based on Circular Dichroism Induced by Helix Formation of Poly[(4-dihydroxyborophenyl)acetylene] , 2001 .

[9]  T. Swager,et al.  Conjugated polymer-based chemical sensors. , 2000, Chemical reviews.

[10]  E. Yashima,et al.  Synthesis and Macromolecular Helicity Induction of a Stereoregular Polyacetylene Bearing a Carboxy Group with Natural Amino Acids in Water , 2000 .

[11]  Stoddart,et al.  Thermoregulated Optical Properties of Peptidic Pseudorotaxanes. , 2000, Angewandte Chemie.

[12]  V. P. Solov'ev,et al.  Crown Ether–Ammonium Complexes: Binding Mechanisms and Solvent Effects , 1999 .

[13]  Katsuhiro Maeda,et al.  Memory of macromolecular helicity assisted by interaction with achiral small molecules , 1999, Nature.

[14]  J. Simonet,et al.  Electroactive polymers containing crown ether or polyether ligands as cation-responsive materials , 1998 .

[15]  Md. Alamgir Hossain,et al.  SEQUENCE-SELECTIVE EVALUATION OF PEPTIDE SIDE-CHAIN INTERACTION. NEW ARTIFICIAL RECEPTORS FOR SELECTIVE RECOGNITION IN WATER , 1998 .

[16]  E. Yashima,et al.  Induced Helix of an Aliphatic Polyacetylene Detected by Circular Dichroism , 1998 .

[17]  R. M. Izatt,et al.  Enantiomeric Recognition of Amine Compounds by Chiral Macrocyclic Receptors. , 1997, Chemical reviews.

[18]  E. Yashima,et al.  Chirality Assignment of Amines and Amino Alcohols Based on Circular Dichroism Induced by Helix Formation of a Stereoregular Poly((4-carboxyphenyl)acetylene) through Acid−Base Complexation , 1997 .

[19]  E. Yashima,et al.  Preparation of polyacetylenes bearing an amino group and their application to chirality assignment of carboxylic acids by circular dichroism , 1997 .

[20]  E. Yashima,et al.  A Stereoregular Polyphenylacetylene Derivative Bearing an Amino Group as a Probe for Chirality Assignments of Acids by Circular Dichroism. , 1996 .

[21]  E. Yashima,et al.  Poly((4-dihydroxyborophenyl)acetylene) as a Novel Probe for Chirality and Structural Assignments of Various Kinds of Molecules Including Carbohydrates and Steroids by Circular Dichroism , 1996 .

[22]  R. M. Izatt,et al.  Thermodynamic and Kinetic Data for Macrocycle Interaction with Cations, Anions, and Neutral Molecules , 1995 .

[23]  E. Yashima,et al.  Poly((4-carboxyphenyl)acetylene) as a Probe for Chirality Assignment of Amines by Circular Dichroism , 1995 .

[24]  T. Satoh,et al.  Cyclopolymerization. Chirality induction for the synthesis of chiroselective corand/ionophore ligands , 1995 .

[25]  R. Nolte,et al.  Biomimetic macromolecular chemistry : design and synthesis of an artificial ion channel based on a polymer containing cofacially stacked crown ether rings. Incorporation in dihexadecyl phosphate vesicles and study of cobalt ion transport , 1992 .

[26]  David Andreu,et al.  A receptor for the enantioselective recognition of phenylalanine and tryptophan under neutral conditions , 1992 .

[27]  Ronald L. Bruening,et al.  Thermodynamic and kinetic data for macrocycle interactions with cations and anions , 1991 .

[28]  N. Voyer.  Preparation of supramolecular devices using peptide synthesis: design and synthesis of a tubular hexa-crown molecule , 1991 .

[29]  J. D. Lamb,et al.  Thermodynamic and kinetic data for cation-macrocycle interaction , 1985 .

[30]  D. Eatough,et al.  The Synthesis and Ion Bindings of Synthetic Multidentate Macrocyclic Compounds. , 1974, Chemical reviews.

[31]  Charles J. Pedersen,et al.  Cyclic polyethers and their complexes with metal salts , 1967 .