4′-O-[2-(2-fluoromalonyl)]-L-tyrosine: A phosphotyrosyl mimic for the preparation of signal transduction inhibitory peptides

Journal of Medicinal Chemistry

Volumn 39, Issue 5, 1996, Pages 1021-1027

  Burke Jr , Terrence R ^a   Ye, Bin ^a   Akamatsu, Miki ^a   Ford Jr , Harry ^a   Yan, Xinjian ^a   Kole, Hemanta K ^b   Wolf, Gert ^c   Shoelson, Steven E ^c   Roller, Peter P ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b NATIONAL INSTITUTE ON AGING   (United States)

^c HARVARD MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 (PHOSPHONOMETHYL)PHENYLALANINE; 4' O (2 FLUORO 2 MALONYL)TYROSINE; INHIBITOR PROTEIN; INSULIN RECEPTOR; O (2 MALONYL)TYROSINE; PROTEIN TYROSINE KINASE; PROTEIN TYROSINE KINASE INHIBITOR; PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHO CELL; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME INHIBITOR INTERACTION; INHIBITION KINETICS; MOLECULAR INTERACTION; MOLECULAR MODEL; NONHUMAN; PROTEIN PROTEIN INTERACTION; SIGNAL TRANSDUCTION;

AMINO ACID SEQUENCE; ANIMALS; CHEMISTRY, PHYSICAL; CRICETINAE; ENZYME INHIBITORS; FLUORINE; HUMANS; IONS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PEPTIDES; PHOSPHOTYROSINE; PROTEIN-TYROSINE-PHOSPHATASE; SIGNAL TRANSDUCTION; SRC HOMOLOGY DOMAINS; TYROSINE;

EID: 0029930442     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950621g     Document Type: Article

References (35)

1. A prelinary account of this work as been presented: Burke, T. R., Jr.; Ye, B.; Akamatsu, M.; Yan, X.; Kole, H. K.; Wolf, G.; Shoelson, S. E.; Koller, P. P. Non phosphorus-containing phosphotyrosyl mimetics amenable to prodrug derivatization and their use in solid-phase peptide synthesis of SH2 domain and phosphatase inhibitors. 209th National American Chemical Society Meeting, Anaheim, CA, April 2-7, 1995; MEDI 14.
2. Boutin, J. A. Tyrosine protein kinase inhibition and cancer. Int. J. Biochem. 1994, 26, 1203-1226.
3. Levitzki, A.; Gazit, A. Tyrosine kinase inhibition: An approach to drug development. Science 1995, 267, 1782-1788.
4. Kavanaugh, W. M.; Williams, L. T. An alternative to SH2 domains for binding tyrosine-phosphorylated proteins. Science 1994, 266, 1862-1865.
5. Bork, P.; Margolis, B. A phosphotyrosine interaction domain. Cell 1995, 80, 693-694.
6. Gustafson, T. A.; He, W. M.; Craparo, A.; Schaub, C. D.; Oneill, T. J. Phosphotyrosine-dependent interaction of SHC and insulin receptor substrate 1 with the NPEY motif of the insulin receptor via a novel non-SH2 domain. Mol. Cell. Biol. 1995, 15, 2500-2508.
7. Eck, M. J. A new flavor in phosphotyrosine recognition. Structure 1995, 3, 421-424.
8. Burke, T. R., Jr. Protein-tyrosine kinase inhibitors. Drugs Future 1992, 17, 119-131.
9. Chang, C. J.; Geahlen, R. L. Protein-Tyrosine Kinase Inhibition - Mechanism-Based Discovery of Antitumor Agents. J. Nat. Prod. Lloydia 1992, 55, 1529-1560.
10. Marseigne, I.; Roques, B. P. Synthesis of new amino acids mimicking sulfated and phosphorylated tyrosine residues. J. Org. Chem. 1988, 53, 3621-3624.
11. Domchek, S. M.; Auger, K. R.; Chatterjee, S.; Burke, T. R., Jr.; Shoelson, S. E. Inhibition of SH2 Domain/Phosphoprotein Association by a Nonhydrolyzable Phosphonopeptide. Biochemistry 1992, 31, 9865-9870.
12. Burke, T. R., Jr.; Smyth, M. S.; Otaka, A.; Nomizu, M.; Roller, P. P.; Wolf, G.; Case, R.; Shoelson, S. E. Nonhydrolyzable phosphotyrosyl mimetics for the preparation of phosphatase-resistant SH2 domain inhibitors. Biochemistry 1994, 33, 6490-6494.
13. Gilmer, T.; Rodriquez, M.; Jordan, S.; Crosby, R.; Alligood, K.; Green, M.; Kimery, M.; Wagner, C.; Kinder, D.; Charifson, P.; Hassell, A. M.; Willard, D.; Luther, M.; Rusnak, D.; Sternbach, D. D.; Mehrotra, M.; Peel, M.; Shampine, L.; Davis, R.; Robbins, J.; Patel, I. R.; Kassel, D.; Burkhart, W.; Moyer, M.; Bradshaw, T.; Berman, J. Peptide inhibitors of src SH3-SH2-phosphoprotein interactions. J. Biol. Chem. 1994, 269, 31711-31719.
14. Chatterjee, S.; Goldstein, B. J.; Csermely, P.; Shoelson, S. E. In Peptides: Chemistry and Biology; Rivier, J. E., Smith, J. A., Eds.; Escom Science Publishers: Leiden, Netherlands, 1992; pp 553-555.
15. Zhang, Z. Y.; Maclean, D.; Mcnamara, D. J.; Sawyer, T. K.; Dixon, J. E. Protein Tyrosine Phosphatase Substrate Specificity - Size and Phosphotyrosine Positioning Requirements in Peptide Substrates. Biochemistry 1994, 33, 2285-2290.
16. Burke, T. R., Jr.; Kole, H. K.; Roller, P. P. Potent inhibition of insulin receptor dephosphorylation by a hexamer peptide containing the phosphotyrosyl mimetic F(2)Pmp. Biochem. Biophys. Res. Commun. 1994, 204, 129-134.
17. Burke, T. R., Jr.; Smyth, M.; Nomizu, M.; Otaka, A.; Roller, P. P. Preparation of fluoro- and hydroxy-4-phosphonomethyl-D,L-phenylalanine suitably protected for solid-phase synthesis of peptides containing hydrolytically stable analogues of O-phosphotyrosine. J. Org. Chem. 1993, 58, 1336-1340.
18. Burke, T. R., Jr.; Nomizu, M.; Otaka, A.; Smyth, M. S.; Roller, P. P.; Case, R. D.; Wolf, G.; Shoelson, S. E. Cyclic peptide inhibitors of phosphatidylinositol 3-kinase p85 SH2 domain binding. Biochem. Biophys. Res. Commun. 1994, 201, 1148-1153.
19. Roller, P. P.; Otaka, A.; Nomizu, M.; Smyth, M. S.; Barchi, J. J., Jr.; Burke, T. R., Jr.; Case, R. D.; Wolf, G.; Shoelson, S. E. Norleucine as a replacement for methionine in phosphatase-resistant linear and cyclic peptides which bind to p85 SH2 domains. Bioorg. Med. Chem. Lett. 1994, 1879-1882.
20. Ye, B.; Burke, T. R., Jr. L-O-Malonyltyrosine (L-OMT) a New Phosphotyrosyl Mimetic Suitably Protected for Solid-Phase Synthesis of Signal Transduction Inhibitory Peptides. Tetrahedron Lett. 1995, 36, 4733-4736.
21. Ye, B.; Akamatsu, M.; Wolf, G.; Shoelson, S. E.; Wolf, G.; Giorgetti-Peraldi, S.; Yan, X.; Roller, P. P.; Burke, T. R., Jr. L-O-(2-Malonyltyrosine: A new phosphotyrosyl mimetic for the preparation of Src homology 2 domain inhibitory peptides. J. Med. Chem. 1995, 38, 4270-4275.
22. Kole, H. K.; Ye, B.; Akamatsu, M.; Yan, X.; Barford, D.; Roller, P. P.; Burke, T. R., Jr. Protein-tyrosine phosphatase inhibition by a peptide containing the phosphotyrosyl mimetic, O-malonyltyrosine (OMT). Biochem. Biophys. Res. Commun. 1995, 209, 817-822.
23. Ledon, H. An improved preparation of alpha-diazocarbonyl compounds. Synthesis 1974, 347-348.
24. Corey, S. D.; Pansegrau, P. D.; Walker, M. C.; Sikorski, J. A. EPSP synthase inhibitor design III. Synthesis & evaluation of a new 5-oxamine acid analog of EPSP which incorporates amalonate ether as a 3-phosphate mimic. Bioorg. Med. Chem. Lett. 1993, 3, 2857-2862.
25. Burke, T. R., Jr.; Smyth, M. S.; Otaka, A.; Roller, P. P. Synthesis of 4-Phosphono(Difluoromethyl)-D,L-Phenylalanine and N-Boc and N-Fmoc Derivatives Suitably Protected for Solid-Phase Synthesis of Nonhydrolyzable Phosphotyrosyl Peptide Analogues. Tetrahedron Lett. 1993, 34, 4125-4128.
26. Unpublished results.
27. Smyth, M. S.; Ford, H., Jr.; Burke, T. R., Jr. A general method for the preparation of benzylic alpha, alpha-difluorophosphonic acids; non-hydrolyzable mimetics of phosphotyrosine. Tetrahedron Lett. 1992, 33, 4137-4140.
28. Burke, T. R., Jr.; Barford, D., manuscript in preparation.
29. Jia, Z. C.; Barford, D.; Flint, A. J.; Tonks, N. K. Structural basis for phosphotyrosine peptide recognition by protein tyrosine phosphatase 1B. Science 1995, 268, 1754-1758.
30. Albericio, F.; Kneib-Cordonier, N.; Biancalana, S.; Gera, L.; Masada, R. I.; Hudson, D.; Barany, G. Preparation and application of the 5-(4-(9-fluorenylmethoxycarbonyl)aminomethyl-3,5-dimethoxyphenoxy)-valeric acid (PAL) handle for the solid-phasesynthesis of C-terminal peptide amides under mild conditions. J. Org. Chem. 1990, 55, 3730-3743.
31. Liotta, A. S.; Kole, H. K.; Fales, H. M.; Roth, J.; Bernier, M. A synthetic tris-sulfotyrosyl dodecapeptide analogue of the insulin receptor 1146-kinase domain inhibits tyrosine dephosphorylation of the insulin receptor in situ. J. Biol. Chem. 1994, 269, 22996-23001.
32. Brillon, D. J.; Henry, R. R.; Klein, H. H.; Olefsky, J. M.; Freidenberg, G. R. Endocrinology 1988, 123, 1837-1847.
33. Piccione, E ; Case, R. D ; Domchek, S. M.; Hu, P.; Chaudhuri, M.; Backer, J. M.; Schlessinger, J.; Shoelson, S. E. Phosphatidylinositol 3-kinase p85 SH2 domain specificity defined by direct phosphopeptide/SH2 domain binding. Biochemistry 1993, 32, 3197-3202.
34. Noyes. Physik Chem. 1893, 11, 495.
35. Gaussian 92. Gaussian, Inc., Carnegie Office Park, Building 6, Pittsburgh, PA 15106.