Synthesis of Novel Linear Multivalent Peptide Ligands Based on the Tetrapeptide MSH(4)

Persistent Link:
http://hdl.handle.net/10150/193421
Title:
Synthesis of Novel Linear Multivalent Peptide Ligands Based on the Tetrapeptide MSH(4)
Author:
Sterne, Robert
Issue Date:
2010
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:
This thesis describes the synthesis of a novel multimeric peptide ligand targeted to the human melanocortin 4 receptor. The synthesis of the peptide was attempted both by solid phase peptide synthesis and by solution phase peptide synthesis, leading to the conclusion that the necessary C- and N- terminal substituents were much easier to install via the solution phase route. The bifunctional peptide was purified and then multimerized in both protected and active amino acid forms using the copper(I)-catalyzed azide alkyne cycloaddition (CuAAC) reaction. The multimers were characterized using MS and UV-Vis spectroscopy. It was found that a large portion of the monomer cyclized under CuAAC conditions, though sufficient multimerization took place to form up to nonamers, as determined by mass spectrometry.
Type:
text; Electronic Thesis
Keywords:
MSH(4); multivalent ligands; peptide synthesis
Degree Name:
M.S.
Degree Level:
masters
Degree Program:
Chemistry; Graduate College
Degree Grantor:
University of Arizona
Advisor:
Mash, Jr., Eugene A
Committee Chair:
Mash, Jr., Eugene A

Full metadata record

DC FieldValue Language
dc.language.isoENen_US
dc.titleSynthesis of Novel Linear Multivalent Peptide Ligands Based on the Tetrapeptide MSH(4)en_US
dc.creatorSterne, Roberten_US
dc.contributor.authorSterne, Roberten_US
dc.date.issued2010en_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.abstractThis thesis describes the synthesis of a novel multimeric peptide ligand targeted to the human melanocortin 4 receptor. The synthesis of the peptide was attempted both by solid phase peptide synthesis and by solution phase peptide synthesis, leading to the conclusion that the necessary C- and N- terminal substituents were much easier to install via the solution phase route. The bifunctional peptide was purified and then multimerized in both protected and active amino acid forms using the copper(I)-catalyzed azide alkyne cycloaddition (CuAAC) reaction. The multimers were characterized using MS and UV-Vis spectroscopy. It was found that a large portion of the monomer cyclized under CuAAC conditions, though sufficient multimerization took place to form up to nonamers, as determined by mass spectrometry.en_US
dc.typetexten_US
dc.typeElectronic Thesisen_US
dc.subjectMSH(4)en_US
dc.subjectmultivalent ligandsen_US
dc.subjectpeptide synthesisen_US
thesis.degree.nameM.S.en_US
thesis.degree.levelmastersen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorMash, Jr., Eugene Aen_US
dc.contributor.chairMash, Jr., Eugene Aen_US
dc.contributor.committeememberGhosh, Indraneelen_US
dc.contributor.committeememberPolt, Robinen_US
dc.identifier.proquest11075en_US
dc.identifier.oclc659755013en_US
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