Synthesis of activity-based probes for protein tyrosine phosphatases with various reporter groups for versatile applications
Date Issued
2009
Date
2009
Author(s)
Chen, Chao-Kai
Abstract
A number of protein tyrosine phosphatases (PTPs) are linked to diseases, ranging from cancers to neurological disorders and diabetes. It was believed that PTPs were involved in controlling the rate and duration of the signal response. The main goal in this thesis is developing different uses of activity-based probes for profiling PTPs in dynamic systems. We designed and synthesized four activity-based probes that carry the same phosphotyrosine analog as a PTP-specific recognition head and a linker that connects the latent trapping device, 2-fluoromethylphenoxyl group, with different reporter groups or affinity tags for visualization and purification. First, a recognition head for PTPs was constructed from tyrosine and linkers with one side carrying an azido group or protected amino group were derived from triethylene glycol. Afterward a precursor of azido-based probe and common intermediates of probes were obtained by coupling the recognition head and linkers. Further, connecting reporter groups of biotin, fluorophore and disulfide-containing linker to the intermediates, and then removing all the allyl protecting groups of phosphates to afford the four probes. All the labeling performance and versatile applications for these probes will be compared to our previous work and evaluated in the future.
Subjects
Protein tyrosine phosphatases (PTPs)
activity-based probes
2-fluoromethylphenoxyl group
biotin
fluorophore
azido group
disulfide
SDGs
Type
thesis
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