TITLE

Chiral resolution of derivatized amino acids using uniformly sized molecularly imprinted polymers in hydro-organic mobile phases

AUTHOR(S)
Haginaka, Jun; Kagawa, Chino
PUB. DATE
April 2004
SOURCE
Analytical & Bioanalytical Chemistry;Apr2004, Vol. 378 Issue 8, p1907
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
Uniformly sized molecularly imprinted polymers (MIPs) for Boc-l-Trp were prepared using ethylene glycol dimethacrylate (EDMA) as the cross-linker, and methacylic acid (MAA) and/or 4-vinylpyridine (4-VPY) as the functional monomers or without use of a functional monomer. The MIPs prepared were evaluated using acetonitrile or a mixture of phosphate buffer and acetonitrile as the mobile phase. The Boc-l-Trp-imprinted EDMA polymers can recognize Boc-l-Trp by its molecular shape, and can thus afford the enantioseparation of Boc-Trp. Besides the molecular shape recognition, the hydrophobic interactions with the polymer backbones as well as the hydrogen-bonding interactions of Boc-l-Trp with carboxyl and pyridyl groups in the polymers should work for the retention and recognition of Boc-l-Trp on the imprinted MAA-co-EDMA and 4-VPY-co-EDMA polymers, respectively, in the hydro-organic mobile phase. The hydrogen-bonding interactions seem to become dominant when only acetonitrile is used as the mobile phase. The Boc-l-Trp-imprinted 4-VPY-co-EDMA polymers gave the highest retentivity and enantioselectivity for Boc-Trp among the MIPs prepared. However, the simultaneous use of MAA and 4-VPY was not effective for the enantioseparation of Boc-Trp in a hydro-organic mobile phase. Furthermore, the baseline separation of Boc-Trp enantiomers was attained within 10 min on the Boc-l-Trp-imprinted 4-VPY-co-EDMA polymers under the optimized HPLC conditions.
ACCESSION #
15124995

 

Related Articles

  • Semiflexible amphiphilic polymers: Cylindrical-shaped, collagenlike, and toroidal structures. Vasilevskaya, Valentina V.; Markov, Vladimir A.; Khalatur, Pavel G.; Khokhlov, Alexei R. // Journal of Chemical Physics;4/14/2006, Vol. 124 Issue 14, p144914 

    A coarse-grained model is used to study the conformational properties of semiflexible polymers with amphiphilic monomer units containing both hydrophilic and hydrophobic interaction sites. The hydrophobically driven conformational transitions are studied using molecular dynamics simulations for...

  • STRONG AND WEAK HYDROGEN BONDS IN Sm/LSm OLIGOMERIC ASSEMBLIES: A COMPARISON OF INTRA- AND INTERCHAIN INTERACTION. ZARIĆ, BOŽIDARKA L.; BUKOROVIĆ, MILICA V.; STOJANOVIĆ, SRĐAN Đ. // Digest Journal of Nanomaterials & Biostructures (DJNB);Apr-Jun2013, Vol. 8 Issue 2, p639 

    The Sm and Sm-like (LSm) proteins are a widespread protein family with members in all kingdoms of life. Sm proteins form complexes engaging in various RNA-processing events. Sm proteins do form and act as oligomeric assemblies whose characteristic is their exceptional stability. This study...

  • Synthesis and characterization of novel optically active poly(ester-imide-imine)s. Hajipour, Abdol Reza; Roosta, Parniyan; Zahmatkesh, Saeed; Ruoho, Arnold E. // e-Polymers;Feb2009, p1 

    N,N′-(3,3′,4,4′-Benzophenonetetracarboxylic)-3,3′,4,4′-diimido-di-L-amino acids (1a-1d) and N,N′-pyromelliticdiimido-di-L-amino acids (2a-2d) are prepared from the reaction of 3,3′,4,4′-benzenetetracarboxylic-3,3′,4,4′-dianhydride or...

  • Solution properties of charged quasi-random copolymers: Integral equation theory. Zherenkova, Lubov V.; Khalatur, Pavel G.; Khokhlov, Alexei R. // Journal of Chemical Physics;10/1/2003, Vol. 119 Issue 13, p6959 

    Using the polymer integral equation method, we study the solution properties of charged quasi-random two-letter (HP) copolymers with two different types of distribution of monomer units along a copolymer chain: proteinlike copolymers and random-block copolymers. The copolymers consist of monomer...

  • Synthesis of Molecularly Imprinted Polymers for Amino Acid Derivates by Using Different Functional Monomers. Scorrano, Sonia; Mergola, Lucia; Del Sole, Roberta; Vasapollo, Giuseppe // International Journal of Molecular Sciences;Mar2011, Vol. 12 Issue 3, p1735 

    Fmoc-3-nitrotyrosine (Fmoc-3-NT) molecularly imprinted polymers (MIPs) were synthesized to understand the influence of several functional monomers on the efficiency of the molecular imprinting process. Acidic, neutral and basic functional monomers, such as acrylic acid (AA), methacrylic acid...

  • Photoluminescence and electron migration characteristics of aromatic poly(amide-imide) containing 1-naphth-aldehyde and 4,4′-diamino diphenyl ether. Khoee, Sepideh; Zamani, Somayeh // e-Polymers;Feb2009, p1 

    A new photoactive polymer poly(amide-imide), was fabricated by reacting two synthesized monomers, N,N′-(4,4′-oxy-bis(4,1-phenylene))-bis-(1,3-dioxo-1,3-dihydroisobenzofuran-5-carbox amide) and N-(4,6-diamino-1,3,5-triazine-2-yl)-1-naphthamide. Polycondensation reaction of the two...

  • Importance of chirality and reduced flexibility of protein side chains: A study with square and tetrahedral lattice models. Jinfeng Zhang; Yu Chen; Rong Chen; Jie Liang // Journal of Chemical Physics;7/1/2004, Vol. 121 Issue 1, p592 

    Side chains of amino acid residues are the determining factor that distinguishes proteins from other unstable chain polymers. In simple models they are often represented implicitly (e.g., by spin states) or simplified as one atom. Here we study side chain effects using two-dimensional square...

  • Production of an anti-complement exo-polymer produced by Auricularia auricula-judae in submerged culture. Sang-Chul Jeong; Sung-Pill Cho; Byung-Keun Yang; Young-Ah Gu; Jin-Ho Jang; Tae-Lin Huh; Chi-Hyun Song // Biotechnology Letters;Jun2004, Vol. 26 Issue 11, p923 

    Exo-polymer (EP) was produced at 1.2 g l-1 in submerged culture of Auricular auricula-judae. Crude EP (AJ-0) has 70% anti-complementary activity (inhibition of total complementary hemolysis 50%; ITCH50). The activating pathway of the complement system occurred through both the classical and...

  • Aptamer base: a collaborative knowledge base to describe aptamers and SELEX experiments. Cruz-Toledo, Jose; McKeague, Maureen; Zhang, Xueru; Giamberardino, Amanda; McConnell, Erin; Francis, Tariq; DeRosa, Maria C.; Dumontier, Michel // Database: The Journal of Biological Databases & Curation;Jan2012, Vol. 2012, p1 

    Over the past several decades, rapid developments in both molecular and information technology have collectively increased our ability to understand molecular recognition. One emerging area of interest in molecular recognition research includes the isolation of aptamers. Aptamers are...

Share

Read the Article

Courtesy of THE LIBRARY OF VIRGINIA

Sorry, but this item is not currently available from your library.

Try another library?
Sign out of this library

Other Topics