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

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

Journal Name: Protein & Peptide Letters

Volume 17 , Issue 7 , 2010

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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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Article Details

VOLUME: 17
ISSUE: 7
Year: 2010
Page: [809 - 816]
Pages: 8
DOI: 10.2174/092986610791306779
Price: $65

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