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Sythesis of the Ligand 1,4,7-Triazacyclononane-Monopropionate for a Potential Manganese Superoxide Dismutase Mimic

Permanent Link: http://ncf.sobek.ufl.edu/NCFE003826/00001

Material Information

Title: Sythesis of the Ligand 1,4,7-Triazacyclononane-Monopropionate for a Potential Manganese Superoxide Dismutase Mimic
Physical Description: Book
Language: English
Creator: Novaes-Card, Simone E.
Publisher: New College of Florida
Place of Publication: Sarasota, Fla.
Creation Date: 2007
Publication Date: 2007

Subjects

Subjects / Keywords: Antioxidant
Enzyme
Biometic
Reactive Oxygen Species
Superoxide
Free Radicals
Genre: bibliography   ( marcgt )
theses   ( marcgt )
government publication (state, provincial, terriorial, dependent)   ( marcgt )
born-digital   ( sobekcm )
Electronic Thesis or Dissertation

Notes

Abstract: Manganese superoxide dismutase is an enzyme found in prokaryotes and in the mitochondria of eukaryotes, where it catalyzes the breakdown of superoxide anion, a harmful free radical produced by cellular respiration. In situations of oxidative stress such as inflammation or ischemia and reperfusion injury, the native enzyme may be unable to keep up with the amount of superoxide generated. Catalytically active, low-molecular-weight synthetic mimics of this enzyme are therefore of great interest as pharmaceuticals. The ligand 1,4,7-triazacyclononane-monopropionate has been proposed as a candidate for complexation with manganese to create a superoxide dismutase mimic. This would provide a geometry similar to that of the active site of the native enzyme, and would also address problems with the geometry of the related 1,4,7-triazacylononane monoacetate manganese complex. Here, a pendant arm addition synthetic route was followed, resulting in successful synthesis of the ligand in small quantities. This product was shown to be pure by carbon nuclear magnetic resonance spectroscopy. It was found that the ligand can be synthesized using either acrylic acid or 3-bromopropionic acid as an electrophile, although 3- bromopropionic acid undergoes elimination to form acrylic acid prior to pendant arm addition. Acrylic acid is thus the more efficient electrophile for use in this reaction. The manganese complex of the ligand remains to be formed and tested to observe its crystal structure and any possible superoxide dismutase ability.
Statement of Responsibility: by Simone E. Novaes-Card
Thesis: Thesis (B.A.) -- New College of Florida, 2007
Electronic Access: RESTRICTED TO NCF STUDENTS, STAFF, FACULTY, AND ON-CAMPUS USE
Bibliography: Includes bibliographical references.
Source of Description: This bibliographic record is available under the Creative Commons CC0 public domain dedication. The New College of Florida, as creator of this bibliographic record, has waived all rights to it worldwide under copyright law, including all related and neighboring rights, to the extent allowed by law.
Local: Faculty Sponsor: Sherman, Suzanne

Record Information

Source Institution: New College of Florida
Holding Location: New College of Florida
Rights Management: Applicable rights reserved.
Classification: local - S.T. 2007 N9
System ID: NCFE003826:00001

Permanent Link: http://ncf.sobek.ufl.edu/NCFE003826/00001

Material Information

Title: Sythesis of the Ligand 1,4,7-Triazacyclononane-Monopropionate for a Potential Manganese Superoxide Dismutase Mimic
Physical Description: Book
Language: English
Creator: Novaes-Card, Simone E.
Publisher: New College of Florida
Place of Publication: Sarasota, Fla.
Creation Date: 2007
Publication Date: 2007

Subjects

Subjects / Keywords: Antioxidant
Enzyme
Biometic
Reactive Oxygen Species
Superoxide
Free Radicals
Genre: bibliography   ( marcgt )
theses   ( marcgt )
government publication (state, provincial, terriorial, dependent)   ( marcgt )
born-digital   ( sobekcm )
Electronic Thesis or Dissertation

Notes

Abstract: Manganese superoxide dismutase is an enzyme found in prokaryotes and in the mitochondria of eukaryotes, where it catalyzes the breakdown of superoxide anion, a harmful free radical produced by cellular respiration. In situations of oxidative stress such as inflammation or ischemia and reperfusion injury, the native enzyme may be unable to keep up with the amount of superoxide generated. Catalytically active, low-molecular-weight synthetic mimics of this enzyme are therefore of great interest as pharmaceuticals. The ligand 1,4,7-triazacyclononane-monopropionate has been proposed as a candidate for complexation with manganese to create a superoxide dismutase mimic. This would provide a geometry similar to that of the active site of the native enzyme, and would also address problems with the geometry of the related 1,4,7-triazacylononane monoacetate manganese complex. Here, a pendant arm addition synthetic route was followed, resulting in successful synthesis of the ligand in small quantities. This product was shown to be pure by carbon nuclear magnetic resonance spectroscopy. It was found that the ligand can be synthesized using either acrylic acid or 3-bromopropionic acid as an electrophile, although 3- bromopropionic acid undergoes elimination to form acrylic acid prior to pendant arm addition. Acrylic acid is thus the more efficient electrophile for use in this reaction. The manganese complex of the ligand remains to be formed and tested to observe its crystal structure and any possible superoxide dismutase ability.
Statement of Responsibility: by Simone E. Novaes-Card
Thesis: Thesis (B.A.) -- New College of Florida, 2007
Electronic Access: RESTRICTED TO NCF STUDENTS, STAFF, FACULTY, AND ON-CAMPUS USE
Bibliography: Includes bibliographical references.
Source of Description: This bibliographic record is available under the Creative Commons CC0 public domain dedication. The New College of Florida, as creator of this bibliographic record, has waived all rights to it worldwide under copyright law, including all related and neighboring rights, to the extent allowed by law.
Local: Faculty Sponsor: Sherman, Suzanne

Record Information

Source Institution: New College of Florida
Holding Location: New College of Florida
Rights Management: Applicable rights reserved.
Classification: local - S.T. 2007 N9
System ID: NCFE003826:00001

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