Synthesis of linear and cyclic phosphopeptides as ligands for the N-terminal SH2-domain of protein tyrosine phosphatase SHP-1

Journal of Peptide Science

Volumn 11, Issue 7, 2005, Pages 390-400

  Imhof, Diana ^a   Nothmann, Doreen ^a   Zoda, Mohammad Safa ^a   Hampel, Kornelia ^a   Wegert, Jenny ^a   Böhmer, Frank D ^a   Reissmann, Siegmund ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Cyclic peptides; Phosphopeptide synthesis; SH2 domain ligands; SHP 1

Indexed keywords

ASPARTIC ACID; CYCLOPEPTIDE; GLUTAMIC ACID; GLYCINE; OCTAPEPTIDE; PHOSPHOPEPTIDE; PHOSPHOTYROSINE; PROTEIN SH2; PROTEIN TYROSINE KINASE; PROTEIN TYROSINE KINASE ROS; PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE SHP 1; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; AMINO TERMINAL SEQUENCE; ARTICLE; BINDING SITE; CONTROLLED STUDY; CYCLIZATION; DEPROTECTION REACTION; DERIVATIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETER; MOLECULAR MODEL; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; RACEMIZATION; SOLID PHASE SYNTHESIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; INTRACELLULAR SIGNALING PEPTIDES AND PROTEINS; LIGANDS; MASS SPECTROMETRY; PEPTIDES, CYCLIC; PHOSPHOPEPTIDES; PROTEIN STRUCTURE, TERTIARY; PROTEIN-TYROSINE-PHOSPHATASE; SHP1 PROTEIN TYROSINE PHOSPHATASE;

EID: 21844441145     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.631     Document Type: Article

References (34)

1. Neel BG, Tonks NK. Protein tyrosine phosphatases in signal transduction. Curr. Opin. Cell Biol. 1997; 9: 193-204.
2. Al-Obeidi FA, Wu JJ, Lam KS. Protein tyrosine kinases: Structure, substrate specificity, and drug discovery. Biopolymers 1998; 47: 197-223.
3. Kuriyan J, Cowburn D. Structures of SH2 and SH3 domains. Curr. Opin. Struct. Biol. 1993; 3: 828-837.
4. Sawyer TK. Src homology-2 domains: structure, mechanisms, and drug discovery. Biopolymers 1998; 47: 243-261.
5. Zhou Y, Abagyan R. How and why phosphotyrosine-containing peptides bind to the SH2 and PTB domains. Fold. Des. 1998; 3: 513-522.
6. Frearson JA, Alexander DR. The role of phosphotyrosine phosphatases in haematopoietic cell signal transduction. BioEssays 1997; 19: 417-427.
7. Neel BG, Gu H, Pao L. The 'Shp'ing news: SH2 domain-containing tyrosine phosphatases in cell signaling. Trends Biochem. Sci. 2003; 28: 284-293.
8. Yang J, Liu L, He D, Song X, Liang X, Zhao ZJ, Zhou GW. Crystal structure of human protein-tyrosine phosphatase SHP-1. J. Biol. Chem. 2003; 278: 6516-6520.
9. Songyang Z, Shoelson SE, Chaudhuri M, Gish G, Pawson T, Haser WG, King F, Roberts T, Ratnofsky S, Lechleider RJ, Neel BG, Birge RB, Fajardo JE, Chou MM, Hanafusa H, Schaffhausen B, Cantley LC. SH2 domains recognize specific phosphopeptide sequences. Cell 1993; 72: 767-778.
10. Beebe KD, Wang P, Arabaci G, Pei D. Determination of the binding specificity of the SH2 domains of protein tyrosine phosphatase SHP-1 through the screening of a combinatorial phosphotyrosyl peptide library. Biochemistry 2000; 39: 13 251-13 260.
11. Cody WL, Lin Z, Panek RL, Rose DW, Rubin JR. Progress in the development of inhibitors of SH2 domains. Curr. Pharm. Des. 2000; 6: 59-98.
12. Biskup C, Böhmer A, Pusch R, Kelbauskas L, Gorshokov A, Majoul I, Lindenau J, Benndorf K, Böhmer FD. Visualization of SHP-1-target interaction. J. Cell Sci. 2004; 117: 5165-5178.
13. Imhof D, Wieligmann K, Hampel K, Nothmann D, Zoda MS, Schmidt-Arras D, Zacharias M, Böhmer FD, Reissmann S. Design and biological activities of linear and cyclic phosphopeptide ligands of the N-terminal SH2 domain of protein tyrosine phosphatase SHP-1. J. Med. Chem. submitted.
14. Müller B, Besser D, Kleinwächter P, Arad O, Reissmann S. Synthesis of N-carboxyalkyl and N-aminoalkyl functionalized dipeptide building units for the assembly of backbone cyclic peptides. J. Peptide Res. 1999; 54: 383-393.
15. Besser D, Müller B, Agricola I, Reissmann S. Synthesis of differentially protected N-acylated reduced pseudodipeptides as building units for backbone cyclic peptides. J. Peptide Sci. 2000; 6: 130-138.
16. Sabatino G, Chelli M, Mazzucco S, Ginanneschi M, Papini AM. Cyclization of histidine containing peptides in the solid-phase by anchoring the imidazole ring to trityl resins. Tetrahedron Lett. 1999; 40: 809-812.
17. Bodanszky M, Bodanszky A. In The Practice of Peptide Synthesis. Akademie Verlag: Berlin, 1985; 109-110.
18. Marfey P. Determination of D-amino acids. II. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene. Carlsberg Res. Commun. 1984; 49: 591-596.
19. Brückner H, Gah C. High-performance liquid chromatographic separation of DL-amino acids derivatized with chiral variants of Sanger's reagent. J. Chromatogr. 1991; 555: 81-95.
20. 2-(5-fluoro-2,4-dinitrophenyl)-L-amino acid amides. Chromatographia 1990; 30: 621-629.
21. McMurray JS, Coleman IV DR, Wang W, Campbell ML. The synthesis of phosphopeptides. Biopolymers 2001; 60: 3-31.
22. Bannwarth W, Trzeciak A. A simple and effective chemical phosphorylation procedure for biomolecules. Helv. Chim. Acta 1987; 70: 175-186.
23. 4-phospho-L-tyrosine-containing peptides. Helv. Chim. Acta 1991; 74: 1314-1328.
24. Bonewald LF, Bibbs L, Kates SA, Khatri A, McMurray JS, Medzihradszky KF, Weintraub ST. Study on the synthesis and characterization of peptides containing phosphorylated tyrosine. J. Peptide Res. 1999; 53: 161-169.
25. 3Bzl,H)-OH. Lett. Pept. Sci. 1999; 6: 91-97.
26. Pascal R, Schmit PO, Mendre C, Dufour MN, Guillon G. Use of diisopropylcarbodiimide in the solid phase synthesis of phosphorylated peptides by the preformed phosphoamino acid building block approach. In Peptides 2000, Martinez J, Fehrentz JA (eds). EDK: Paris, 2001; 263-264.
27. White P. Optimization of coupling methods for the introduction of mono-benzyl phosphate esters of Fmoc protected phosphoamino acids. In Peptides: The Wave of the Future, Lebl M, Houghten RA (eds). Kluwer Academic: Norwell, 2001; 97-98.
28. Nomizu M, Otaka A, Burke Jr TR, Roller PP. Synthesis of phosphonomethyl-phenylalanine and phosphotyrosine containing cyclic peptides as inhibitors of protein tyrosine kinase/SH2 interactions. Tetrahedron 1994; 50: 2691-2702.
29. Burke TR, Nomizu M, Otaka A, Smyth MS, Roller PP, Case RD, Wolf G, Shoelson SE. Cyclic peptide inhibitors of phophatidylinositol 3-kinase p85 SH2 domain binding. Biochem. Biophys. Res. Commun. 1994; 201: 1148-1153.
30. 2. Arch. Biochem. Biophys. 1998; 355: 124-130.
31. Oligino L, Lung FDT, Sastry L, Bigelow J, Cao T, Curran M, Burke Jr TR, Wang S, Krag D, Roller PP, King CR. Nonphosphorylated peptide ligands for the Grb2 Src homology 2 domain. J. Biol. Chem. 1997; 272: 29 046-29 052.
32. Li P, Peach ML, Zhang M, Liu H, Yang D, Nicklaus M, Roller PP. Structure-based design of thioether-bridged cyclic phosphopeptides binding to Grb2-SH2 domain. Bioorg. Med. Chem. Lett. 2003; 13: 895-899.
33. Besser D, Müller B, Kleinwächter P, Greiner G, Seyfarth L, Steinmetzer T, Arad O, Reissmann S. Synthesis and characterization of octapeptide somatostatin analogues with backbone cyclization: Comparison of different strategies, biological activities and enzymatic stabilities. J. Prakt. Chem. 2000; 342: 537-545.
34. Arold H, Reissmann S. Synthesis of bradykinin analogues containing threo-β-phenyl serine. J. Prakt. Chem. 1970; 312: 1130-1144.