Synthesis of 5-Fluoroproline Derivatives,
Abstract
Cyclophilin, a major cytosolic binding protein, is the first peptidyl-prolyl cis-trans isomerase (PPIase) identified. this enzyme catalyzes cis-trans isomerization of X-Pro bonds, an isomerization that may be a rate limiting step in some protein-folding reactions, and that may correlate with the immunosuppressive activity of the drug, Cyclosporin-A. Fluoroproline (5-FPro, 1), which has not been reported previously, is expected to be unstable due to the potential for imine formulation. Hypothesizing that acyl derivatives of 5-FPro might be sufficiently stable to be assayed as inhibitors of PPIase, due to the delocalization of the lone pair of electrons on nitrogen into the adjacent carbonyl group, we have synthesized a series of 5-FPro-containing substrates.
Document Details
- Document Type
- Technical Report
- Publication Date
- Jan 01, 1992
- Accession Number
- ADP008548
Entities
People
- Daniel H. Rich
- James L. Kofron
- John R. Kagel
Organizations
- University of Wisconsin–Madison