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SYNTHESIS OF FMOC-GLY-VAL PHOSPHINIC PSEUDODIPEPTIDE BUILDING BLOCK FOR PRODUCTION OF TRIPLE-HELICAL PEPTIDE INHIBITORS OF MATRIX METALLOPROTEINASE-2 AND -9

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Date Issued:
2022
Abstract/Description:
Capable of reshaping the extracellular matrix, matrix metalloproteinases (MMPs) are of enormous consequence to human health. The pathologies of cancers and diseases of the skeletal, central nervous, and cardiovascular systems often owe to the overactivity of MMPs. While efforts to produce therapeutic inhibitors have been largely unsuccessful, triple-helical peptide inhibitors (THPIs) of MMPs show tremendous potential. The synthesis of phosphinic pseudodipeptide building blocks needed for THPIs is entirely replicable and convenient. Here we replicate a crucial step in the synthesis, the cascade bis-deprotection, and formation of Fmoc-amine. The procedure’s feasibility is demonstrated through a 77% yield of the Fmoc-Gly-Val phosphinic pseudodipeptide building block to be incorporated into THPIs of the gelatinases. In the future, it is hoped that such procedures will culminate in large-scale production of refined THPIs, enabling in-depth biochemical studies, further optimization, clinical trials, and novel therapeutics.
Title: SYNTHESIS OF FMOC-GLY-VAL PHOSPHINIC PSEUDODIPEPTIDE BUILDING BLOCK FOR PRODUCTION OF TRIPLE-HELICAL PEPTIDE INHIBITORS OF MATRIX METALLOPROTEINASE-2 AND -9.
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Name(s): Deutsch, Michael H., author
Fields, Gregg B. , Thesis advisor
Harriet L. Wilkes Honors College
Florida Atlantic University, Degree grantor
Type of Resource: text
Genre: Thesis
Date Created: 2022
Date Issued: 2022
Publisher: Florida Atlantic University
Place of Publication: Jupiter, Florida
Physical Form: application/pdf
Extent: 28 p.
Language(s): English
Abstract/Description: Capable of reshaping the extracellular matrix, matrix metalloproteinases (MMPs) are of enormous consequence to human health. The pathologies of cancers and diseases of the skeletal, central nervous, and cardiovascular systems often owe to the overactivity of MMPs. While efforts to produce therapeutic inhibitors have been largely unsuccessful, triple-helical peptide inhibitors (THPIs) of MMPs show tremendous potential. The synthesis of phosphinic pseudodipeptide building blocks needed for THPIs is entirely replicable and convenient. Here we replicate a crucial step in the synthesis, the cascade bis-deprotection, and formation of Fmoc-amine. The procedure’s feasibility is demonstrated through a 77% yield of the Fmoc-Gly-Val phosphinic pseudodipeptide building block to be incorporated into THPIs of the gelatinases. In the future, it is hoped that such procedures will culminate in large-scale production of refined THPIs, enabling in-depth biochemical studies, further optimization, clinical trials, and novel therapeutics.
Identifier: FAUHT00194 (IID)
Degree granted: Thesis (B.S.)--Florida Atlantic University, Harriet L. Wilkes Honors College, 2022
Persistent Link to This Record: http://purl.flvc.org/fau/fd/FAUHT00194
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Host Institution: FAU
Is Part of Series: Florida Atlantic University Digital Library Collections.

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