Synlett 2017; 28(15): 1950-1955
DOI: 10.1055/s-0036-1588225
cluster
© Georg Thieme Verlag Stuttgart · New York

Synthetic Approach to Argpyrimidine as a Tool for Investigating Nonenzymatic Posttranslational Modification of Proteins

Maria Matveenko, Christian F. W. Becker*
  • University of Vienna, Department of Chemistry, Institute of Biological Chemistry, Währinger Strasse 38, 1090 Vienna, Austria   Email: christian.becker@univie.ac.at
Supported by: Austrian Academy of Sciences (APART fellowship)
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Publication History

Received: 24 January 2017

Accepted after revision: 12 March 2017

Publication Date:
19 April 2017 (eFirst)

Published as part of the Cluster Recent Advances in Protein and Peptide Synthesis

Abstract

Nonenzymatic posttranslational modifications (nPTMs) of proteins are involved in age-related, metabolic and other diseases and need to be investigated at the molecular level. Here, we describe how we used organic synthesis to enable the study of the effect of argpyrimidine (Apy), an nPTM that forms at arginine residues, on one of its target proteins. We developed an efficient approach to Apy as a universal building block for Fmoc-based solid-phase peptide synthesis that allows for the construction of peptides containing this nPTM in predetermined positions. Moreover, a straightforward one-step synthesis of protecting-group-free Apy was achieved, which enabled the preparation of gram-quantities of this noncanonical amino acid that can serve as a biomarker or a feedstock in construction of Apy-containing proteins via the expanded genetic code methods.

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