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

Author

• Michael H. Deutsch

Date of Award

2022

Document Type

Dissertation/Thesis

Submission Date

October 2026

Thesis/Dissertation Advisor [Chair]

Fields, Gregg B.

Abstract

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.

Comments

Thesis (B.S.)--Florida Atlantic University, Harriet L. Wilkes Honors College, 2022

Recommended Citation

Deutsch, Michael H., "SYNTHESIS OF FMOC-GLY-VAL PHOSPHINIC PSEUDODIPEPTIDE BUILDING BLOCK FOR PRODUCTION OF TRIPLE-HELICAL PEPTIDE INHIBITORS OF MATRIX METALLOPROTEINASE-2 AND -9" (2022). Harriet L Wilkes Honors College Theses 2020 - Present. 155.
https://digitalcommons.fau.edu/etd_honors/155

Extent

28 p.

Identifier

FAUHT00194