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Synthetic Strategies to a Backbone-Side Chain Cyclic SHP-1 N-SH2 Ligand Containing N-Functionalized Alkyl Phosphotyrosine

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The cyclic peptide EGLNcΨ[CON((CH2)3NH)pYNleE(NHCH2CO)]L-NH2 (1) was designed and synthesized according to a native interaction partner of tyrosine phosphatase SHP-1. We introduced N-aminopropyl-phosphotyrosine to enable backbone-side chain cyclization with a glutamic acid derivative as counterpart for cyclization. Different approaches have been compared to find a strategy for the generation of backbone and backbone-side chain cyclic phosphopeptides.

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Keywords: N-functionalized alkyl phosphotyrosine; SH2 domain; SHP-1; backbone cyclization; ligand; protein tyrosine phosphatase

Document Type: Research Article

Publication date: 2010-07-01

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  • Protein & Peptide Letters publishes short papers in all important aspects of protein and peptide research, including structural studies, recombinant expression, function, synthesis, enzymology, immunology, molecular modeling, drug design etc. Manuscripts must have a significant element of novelty, timeliness and urgency that merit rapid publication. Reports of crystallisation, and preliminary structure determinations of biologically important proteins are acceptable. Purely theoretical papers are also acceptable provided they provide new insight into the principles of protein/peptide structure and function.
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