Synthetic strategies to a backbone-side chain cyclic SHP-1 N-SH2 ligand containing N-functionalized alkyl phosphotyrosine.
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.
Teichmann
Kathleen
K
Center for Molecular Biomedicine, Department of Biochemistry, Peptide Chemistry Group, Friedrich-Schiller-University, Hans-Knöll-Str. 2, D-07745 Jena, Germany.
Niksch
Tobias
T
Wieligmann
Karin
K
Zacharias
Martin
M
Imhof
Diana
D
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
D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010456:Peptides, Cyclic; D019000:Phosphotyrosine; D053824:Protein Tyrosine Phosphatase, Non-Receptor Type 6