Synthesis of a novel peptidic photoaffinity probe for the PTP-1B enzyme.

The synthesis of a novel radioactive peptidic photoaffinity probe for the PTP-1B enzyme as well as some SAR leading to the choice of this compound as a photoaffinity probe are presented.

[1]  F. Richards,et al.  3-Trifluoromethyl-3-phenyldiazirine. A new carbene generating group for photolabeling reagents. , 1980, The Journal of biological chemistry.

[2]  E. Asante-Appiah,et al.  The development of potent non-peptidic PTP-1B inhibitors. , 2004, Bioorganic & medicinal chemistry letters.

[3]  R. Zamboni,et al.  3,6-Fluorescein Diphosphate: A Sensitive Fluorogenic and Chromogenic Substrate for Protein Tyrosine Phosphatases , 1999, Journal of biomolecular screening.

[4]  B. Jallal,et al.  Protein tyrosine phosphatases: their role in insulin action and potential as drug targets. , 1999, Expert opinion on investigational drugs.

[5]  D. Solas,et al.  An Efficient Synthesis of N-α-Fmoc-4-(Phosphonodifluoromethyl)-l- phenylalanine , 1996 .

[6]  J. Chernoff,et al.  Protein-Tyrosine Phosphatase 1B Complexes with the Insulin Receptor in Vivo and Is Tyrosine-phosphorylated in the Presence of Insulin* , 1997, The Journal of Biological Chemistry.

[7]  R. Zamboni,et al.  A novel photoaffinity probe for the LTD4 receptor. , 1998, Bioorganic & Medicinal Chemistry.

[8]  B. Kennedy,et al.  Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene. , 1999, Science.

[9]  Jean Martínez,et al.  Enantioselective Synthesis of γ-Hydroxynorvaline , 1997 .

[10]  C. R. Kahn,et al.  Insulin Action, Diabetogenes, and the Cause of Type II Diabetes , 1994, Diabetes.

[11]  P. Roller,et al.  Potent inhibition of insulin receptor dephosphorylation by a hexamer peptide containing the phosphotyrosyl mimetic F2Pmp. , 1994, Biochemical and biophysical research communications.

[12]  Jerrold M. Olefsky,et al.  Protein-tyrosine Phosphatase 1B Is a Negative Regulator of Insulin- and Insulin-like Growth Factor-I-stimulated Signaling* , 1996, The Journal of Biological Chemistry.

[13]  J. Meyerovitch,et al.  Osmotic Loading of Neutralizing Antibodies Demonstrates a Role for Protein-tyrosine Phosphatase 1B in Negative Regulation of the Insulin Action Pathway (*) , 1995, The Journal of Biological Chemistry.