title: Synthetic strategies to a backbone-side chain cyclic SHP-1 N-SH2 ligand containing N-functionalized alkyl phosphotyrosine.
abstract: The cyclic peptide EGLNc Psi [CON((CH(2))(3)NH)pYNleE(NHCH(2)CO)]L-NH(2) (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.
authors.affiliation: Center for Molecular Biomedicine, Department of Biochemistry, Peptide Chemistry Group, Friedrich-Schiller-University, Hans-Knöll-Str. 2, D-07745 Jena, Germany.
authors.forename: Kathleen
authors.initials: K
authors.lastname: Teichmann
authors.forename: Tobias
authors.initials: T
authors.lastname: Niksch
authors.forename: Karin
authors.initials: K
authors.lastname: Wieligmann
authors.forename: Martin
authors.initials: M
authors.lastname: Zacharias
authors.forename: Diana
authors.initials: D
authors.lastname: Imhof
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D005449:Fluorenes / Q000737:chemistry / Q000378:metabolism; D008958:Models, Molecular; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000378:metabolism; D019000:Phosphotyrosine / Q000737:chemistry* / Q000378:metabolism; D053824:Protein Tyrosine Phosphatase, Non-Receptor Type 6 / Q000737:chemistry* / Q000378:metabolism; D018909:src Homology Domains
chemical_list: D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010456:Peptides, Cyclic; D019000:Phosphotyrosine; D053824:Protein Tyrosine Phosphatase, Non-Receptor Type 6