I. Use of 9-methylfluorene as an indicator for organometallic titrations II. Synthesis of a branched polyethylene glycol linker for peptide ligands III. Synthesis of a linker for peptide ligands and a study of its pH sensitivity

Persistent Link:
http://hdl.handle.net/10150/290107
Title:
I. Use of 9-methylfluorene as an indicator for organometallic titrations II. Synthesis of a branched polyethylene glycol linker for peptide ligands III. Synthesis of a linker for peptide ligands and a study of its pH sensitivity
Author:
Bowen, Martina E.
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:
This work details the synthesis of some useful organic molecules: (I) 9-Methylfluorene was tested as an indicator in the titration of commonly used organometallic reagents. This indicator is readily prepared in three steps from fluorenone. In THF solution the deprotonated indicator is red and exhibits a sharp endpoint. The highly basic reagents sec-butyllithium and tert -butyllithium can be titrated in ether solution, where the color of the deprotonated indicator is yellow. (II) A branched, polyethylene glycol based linker for peptide ligands was designed and synthesized. The linker needed to be water soluble, to be stable under both acidic and basic conditions, to have amine and carboxyl termini for use in solid phase peptide synthesis, and to have an attachment site for a fluorescent marker. The polyethylene glycol linker was designed with a carboxyl terminus and two amine termini that can be differentially protected to facilitate selective deprotection and reaction with three peptides or two peptides and a fluorescent tag. (III) A molecule containing a linear polyethylene glycol linker with beta-alkoxyamide moiety was synthesized and its pH stability determined using an HPLC method. Stability was assayed in 5 mM buffers at pH 4, 7, and 9 over 24 hours. No decomposition in these solutions was detected. The linker was then subjected to 10 mM acid or base solution and analyzed over 24 hours. Again, no decomposition was observed.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Chemistry, Biochemistry.; Chemistry, Organic.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Mash, Eugene A., Jr.

Full metadata record

DC FieldValue Language
dc.language.isoen_USen_US
dc.titleI. Use of 9-methylfluorene as an indicator for organometallic titrations II. Synthesis of a branched polyethylene glycol linker for peptide ligands III. Synthesis of a linker for peptide ligands and a study of its pH sensitivityen_US
dc.creatorBowen, Martina E.en_US
dc.contributor.authorBowen, Martina E.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.abstractThis work details the synthesis of some useful organic molecules: (I) 9-Methylfluorene was tested as an indicator in the titration of commonly used organometallic reagents. This indicator is readily prepared in three steps from fluorenone. In THF solution the deprotonated indicator is red and exhibits a sharp endpoint. The highly basic reagents sec-butyllithium and tert -butyllithium can be titrated in ether solution, where the color of the deprotonated indicator is yellow. (II) A branched, polyethylene glycol based linker for peptide ligands was designed and synthesized. The linker needed to be water soluble, to be stable under both acidic and basic conditions, to have amine and carboxyl termini for use in solid phase peptide synthesis, and to have an attachment site for a fluorescent marker. The polyethylene glycol linker was designed with a carboxyl terminus and two amine termini that can be differentially protected to facilitate selective deprotection and reaction with three peptides or two peptides and a fluorescent tag. (III) A molecule containing a linear polyethylene glycol linker with beta-alkoxyamide moiety was synthesized and its pH stability determined using an HPLC method. Stability was assayed in 5 mM buffers at pH 4, 7, and 9 over 24 hours. No decomposition in these solutions was detected. The linker was then subjected to 10 mM acid or base solution and analyzed over 24 hours. Again, no decomposition was observed.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectChemistry, Biochemistry.en_US
dc.subjectChemistry, Organic.en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorMash, Eugene A., Jr.en_US
dc.identifier.proquest3145047en_US
dc.identifier.bibrecord.b47209902en_US
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