Download the full-sized PDF of Synthesis of a phosphotyrosine analog, BrPmp and its incorporation into peptidesDownload the full-sized PDF



Permanent link (DOI):


Export to: EndNote  |  Zotero  |  Mendeley


This file is in the following communities:

Graduate Studies and Research, Faculty of


This file is in the following collections:

Theses and Dissertations

Synthesis of a phosphotyrosine analog, BrPmp and its incorporation into peptides Open Access


Other title
Type of item
Degree grantor
University of Alberta
Author or creator
Tulsi, Naresh Singh
Supervisor and department
Examining committee member and department
Department of Chemistry

Date accepted
Graduation date
Master of Science
Degree level
Protein tyrosine phosphatases (PTPs) are important therapeutic targets for medicinal chemists and biochemists. General strategies for the development of inhibitors of these enzymes are needed. One known inhibitor of PTPs are analogs containing the α-bromobenzylphosphonate (BBP) motif. We hypothesized that the BBP functional group could be used to develop targeted PTP inhibitors, by incorporation into peptide sequences. Using model compounds, we first tested the stability of the BBP motif to solid phase peptide synthesis (SPPS) conditions. A scaleable synthetic methodology was then developed for generating an amino acid analog that incorporates the BBP functional group. Enzyme inhibition studies with the PTP CD45 demonstrated that the BBP amino acid derivatives were irreversible inhibitors. Using the Fmoc protected BrPmp BBP amino acid, we then incorporated it into longer peptide sequences. We were able to generate a short series of nonapeptides that incorporated BrPmp and identify areas of the chemistry which required improvement.
License granted by Naresh Tulsi ( on 2011-01-12T01:43:26Z (GMT): Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of the above terms. The author reserves all other publication and other rights in association with the copyright in the thesis, and except as herein provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
Citation for previous publication

File Details

Date Uploaded
Date Modified
Audit Status
Audits have not yet been run on this file.
File format: pdf (Portable Document Format)
Mime type: application/pdf
File size: 906939
Last modified: 2015:10:12 16:35:45-06:00
Filename: Tulsi_Naresh_Spring 2011.pdf
Original checksum: bf1f892a9316e0af2061d905ba486c55
Well formed: false
Valid: false
Status message: Invalid page tree node offset=447853
Status message: Unexpected error in findFonts java.lang.ClassCastException: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject cannot be cast to edu.harvard.hul.ois.jhove.module.pdf.PdfDictionary offset=2795
Status message: Invalid Annotation list offset=863291
Status message: Outlines contain recursive references.
File title: Chapter 1: Inhibitors of PTPs
Activity of users you follow
User Activity Date