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Synthesis of Mono-ADP-Ribosylated Oligopeptides Using Ribosylated Amino Acid Building Blocks
journal contribution
posted on 2010-04-14, 00:00 authored by Gerbrand J. van der Heden van Noort, Maarten G. van der Horst, Herman S. Overkleeft, Gijsbert A. van der Marel, Dmitri V. FilippovAdenosine diphosphate ribosylation (ADP-ribosylation) is a widely occurring post-translational modification of proteins at nucleophilic side chains of amino acid residues, such as asparagine, glutamic acid, and arginine. Elucidation of the biological role of ADP-ribosylation events would benefit from the availability of well-defined ADP-ribosylated peptides. Main issues in the construction of synthetic ADP-ribosylated peptides involve the availability of protected ribosylated amino acids suitable for peptide synthesis, development of a protective group strategy for peptide fragments compatible with the integrity of the adenosine diphosphate moiety, and an efficient procedure for pyrophosphate formation. In this paper we present a first approach to the chemical synthesis of ADP-ribosylated peptides in solution and on solid support. We describe an efficient synthesis of suitably protected ribosylated asparagine and glutamine building blocks suitable for Fmoc-based peptide synthesis. We further demonstrate a successful application of these ribosylated amino acids in the assembly of three fully synthetic ADP-ribosylated peptides by solution and solid phase approaches.
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- Biochemistry
- Molecular Biology
- Biotechnology
- Environmental Sciences not elsewhere classified
- Chemical Sciences not elsewhere classified
- Astronomical and Space Sciences not elsewhere classified
- Immunology
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- Infectious Diseases
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