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ARTIFICIAL RECEPTORS FOR MOLECULAR RECOGNITION OF AMINO ACIDS, PEPTIDES AND CARBOHYDRATES

SMUKSTE, INESE
http://rave.ohiolink.edu/etdc/view?acc_num=ucin1029757614

Abstract Details

2002, PhD, University of Cincinnati, Arts and Sciences : Chemistry.
A convenient method for creating neutrally charged, water soluble calix[4]arenes that contain hydroxyamides attached to their lower rims has been developed; selective amidation reactions of a diacid calix[4]arene with several unprotected hydroxyamines was achieved using EEDQ as the coupling agent. The solubilities of the derivatized calix[4]arenes depended on the structure of the hydroxyamide, as well as, the number of hydroxyl groups. Molecular simulations of the derivatized compounds in water revealed that intramolecular H-bond formation is an important component of solubility. Calix[4]arenes containing ten hydroxyl groups were as soluble in water as a calix[4]arene that contained two carboxylates. Dialkylammonium templated self-assembled association has been used to synthesize DCC-rotaxanes; N-Boc protected diaminobenzo[24]crown-8 and 5-(3,5-di- tert -butyl-benzylamino)-pentanoic acid hexafluorophosphate salt form a self-assembled complex in chloroform, which is mechanically locked by reacting with DCC. N -Boc protected DCC-rotaxane was used to synthesize phenylalanine and di- p -phenylcalix[4]arene host-[2]rotaxanes. Upon deprotection, corresponding amino host-[2]rotaxanes were obtained in high yields and used for synthesis of artificial receptors. N -acetyl-arginine derivatized di- p -phenylcalix[4]arenes and N -acetyl-arginine derivatized host-[2]rotaxanes were prepared and their ability to perform as artificial receptors was studied. Rotaxane receptors bound N -acetyl protected amino acid carboxylates much stronger than calix[4]arene receptors containing same functional groups. N -acetyl-arginine and glutaric acid derivatized phenylalanine host-[2]rotaxanes were prepared and their structure-function relationship was studied in detail. A relative measure of the intramolecular interaction energies between the functional groups in DMSO-water mixtures was obtained by comparing their pK a ’s. Rotaxane structures were investigated through 2D-NMR analysis and molecular dynamics simulations. Association constants for complexes of these rotaxanes and amino acids were determined in a variety of solvent systems by 1 H NMR analysis.
Dr. David Smithrud (Advisor)
122 p.
Chemistry, Organic
CALIX[4]ARENES; HOST-ROTAXANES; HOST-GUEST CHEMISTRY; SELF-ASSEMBLY

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Citations

  • SMUKSTE, I. (2002). ARTIFICIAL RECEPTORS FOR MOLECULAR RECOGNITION OF AMINO ACIDS, PEPTIDES AND CARBOHYDRATES [Doctoral dissertation, University of Cincinnati]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1029757614

    APA Style (7th edition)

  • SMUKSTE, INESE. ARTIFICIAL RECEPTORS FOR MOLECULAR RECOGNITION OF AMINO ACIDS, PEPTIDES AND CARBOHYDRATES. 2002. University of Cincinnati, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ucin1029757614.

    MLA Style (8th edition)

  • SMUKSTE, INESE. "ARTIFICIAL RECEPTORS FOR MOLECULAR RECOGNITION OF AMINO ACIDS, PEPTIDES AND CARBOHYDRATES." Doctoral dissertation, University of Cincinnati, 2002. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1029757614

    Chicago Manual of Style (17th edition)

ucin1029757614
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© 2002, all rights reserved.
This open access ETD is published by University of Cincinnati and OhioLINK.