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

Kathleen      Teichmann; Tobias      Niksch; Karin      Wieligmann; Martin      Zacharias; Diana      Imhof

Abstract

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.

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

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Protein & Peptide Letters

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

Volume: 17 Issue: 7

Author(s): Kathleen Teichmann, Tobias Niksch, Karin Wieligmann, Martin Zacharias and Diana Imhof

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

Abstract: 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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Teichmann Kathleen, Niksch Tobias, Wieligmann Karin, Zacharias Martin and Imhof Diana, Synthetic Strategies to a Backbone-Side Chain Cyclic SHP-1 N-SH2 Ligand Containing N-Functionalized Alkyl Phosphotyrosine, Protein & Peptide Letters 2010; 17 (7) . https://dx.doi.org/10.2174/092986610791306779