The design and synthesis of imine-bridged cyclic peptides andthe solid phase synthesis of β-turn mimetics

Persistent Link:
http://hdl.handle.net/10150/291597
Title:
The design and synthesis of imine-bridged cyclic peptides andthe solid phase synthesis of β-turn mimetics
Author:
Andrus, Danice M.
Issue Date:
2004
Publisher:
The University of Arizona.
Rights:
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
Abstract:
Pain is perhaps the most unpleasant sensation humans experience. While pain is important in preventing further injury and as a detection mechanism for ill-health; effective relief of pain, especially chronic or neuropathic, is a critical quality of life issue. As discoveries are made regarding opioid receptor-acceptor-ligand interactions, ligands that bind specifically to a receptor subtype can modify behavior without triggering side effects. Topographical space control is an important consideration in ligand design. According to Ramachandran¹, α-amino acids are confined to the following low-energy conformations, α-helix, β-sheets, extended structures, and β-turns. Endogenous peptides such as the enkephalins and endomorphins activate the opioid receptor subtypes, δ- and μ-, respectively, and are involved in the pain cascade. Research herein concerns the synthesis of δ-opioid peptidomimetics that replace the Gly-Gly unit of Leu-enkephalins with a β-turn mimetic moiety. Additionally, using the bioactive nostocyclopeptolides as templates, smaller cyclized imino-bridged peptides were designed. These peptides were developed with the mu-opioid subtype requirements in mind.
Type:
text; Thesis-Reproduction (electronic)
Keywords:
Chemistry, Organic.
Degree Name:
M.S.
Degree Level:
masters
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Hruby, Victor J.

Full metadata record

DC FieldValue Language
dc.language.isoen_USen_US
dc.titleThe design and synthesis of imine-bridged cyclic peptides andthe solid phase synthesis of β-turn mimeticsen_US
dc.creatorAndrus, Danice M.en_US
dc.contributor.authorAndrus, Danice M.en_US
dc.date.issued2004en_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en_US
dc.description.abstractPain is perhaps the most unpleasant sensation humans experience. While pain is important in preventing further injury and as a detection mechanism for ill-health; effective relief of pain, especially chronic or neuropathic, is a critical quality of life issue. As discoveries are made regarding opioid receptor-acceptor-ligand interactions, ligands that bind specifically to a receptor subtype can modify behavior without triggering side effects. Topographical space control is an important consideration in ligand design. According to Ramachandran¹, α-amino acids are confined to the following low-energy conformations, α-helix, β-sheets, extended structures, and β-turns. Endogenous peptides such as the enkephalins and endomorphins activate the opioid receptor subtypes, δ- and μ-, respectively, and are involved in the pain cascade. Research herein concerns the synthesis of δ-opioid peptidomimetics that replace the Gly-Gly unit of Leu-enkephalins with a β-turn mimetic moiety. Additionally, using the bioactive nostocyclopeptolides as templates, smaller cyclized imino-bridged peptides were designed. These peptides were developed with the mu-opioid subtype requirements in mind.en_US
dc.typetexten_US
dc.typeThesis-Reproduction (electronic)en_US
dc.subjectChemistry, Organic.en_US
thesis.degree.nameM.S.en_US
thesis.degree.levelmastersen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorHruby, Victor J.en_US
dc.identifier.proquest1420170en_US
dc.identifier.bibrecord.b46709009en_US
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