3-(3'-Fluorenyl-9'-oxo)-L-alanine: A novel photoreactive conformationally constrained amino acid

Journal of Peptide Research

Volumn 55, Issue 3, 2000, Pages 230-239

  Han, Y ^a   Bisello, A ^a   Nakamoto, C ^a   Rosenblatt, M ^a   Chorev, Michael ^a,b  

^a BETH ISRAEL DEACONESS MEDICAL CENTER   (United States)

^b HARVARD MEDICAL SCHOOL   (United States)

Author keywords

3 (3' fluorenyl 9' oxo) L alanine; Amino acid synthesis; Arylketones; Human PTH1 receptor; Parathyroid hormone; Photoaffinity labeling; Photoreactive amino acid

Indexed keywords

3 (3' FLUORENYL 9' OXO)ALANINE; 9 FLUORENONE 3 CARBOXYLIC ACID; ALANINE DERIVATIVE; AMINO ACID DERIVATIVE; BENZOPHENONE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; G PROTEIN COUPLED RECEPTOR; HORMONE RECEPTOR STIMULATING AGENT; LIGAND; PARATHYROID HORMONE; PARATHYROID HORMONE RECEPTOR; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; CONTROLLED STUDY; CROSS LINKING; HUMAN; HUMAN CELL; KIDNEY CELL; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ALANINE; CELL LINE; CROSS-LINKING REAGENTS; FLUORENES; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PARATHYROID HORMONE; PHOTOAFFINITY LABELS; PHOTOLYSIS; RECEPTORS, PARATHYROID HORMONE;

EID: 0033998541     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.2000.00175.x     Document Type: Article

References (46)

1. B25 insulins: photoactivatable analogues that quantitatively cross-link, radiolabel, and activate the insulin receptor. J. Biol. Chem. 268, 5361-5364.
2. 2. Fleming, S.A. (1995) Chemical reagents in photoaffinity labeling. Tetrahedron 57, 12479-12520.
3. 3. Fleet, G.W.J., Porter, R.R. & Knowles, J.R. (1969) Affinity labeling of antibodies with aryl nitrene as reactive group. Nature 224, 511-512.
4. 4. Singh, A., Thorton, E.R. & Westheimer, F.H. (1962) The photolysis of diazoacetylchymotrypsin. J. Biol. Chem. 237, 3007-3008.
5. 5. Smith, R.A. & Knowles, J.R. (1973) Aryldiazirines. Potential reagents for photolabeling of biological receptor sites. J. Am. Chem. Soc. 95, 5072-5073.
6. 6. Galardy, R.E., Craig, L.C. & Printz, M.P. (1973) Benzophenone triplet: a new photochemical probe of biological ligand-receptor interactions. Nature 242, 127-128.
7. 7. Dorman, G. & Prestwich, G.D. (1994) Benzophenone photophores in biochemistry. Biochemistry 33, 5661-5673.
8. 8. Wess, J., Gdula, D. & Brann, M.R. (1991) Site-directed mutagenesis of the m3 muscarinic receptor: identification of a series of threonine and tyrosine residues involved in agonist but not antagonist binding. EMBO J. 10, 3729-3734.
9. 9. Girault, S., Sagan, S., Bolbach, G., Lavielle, S. & Chassaing, G. (1996) The use of photolabeled peptides to localize the substance-P-binding site in the human neurokinin-1 tachykinin receptor. Eur. J. Biochem. 240, 215-222.
10. 10. Zhou, A.T., Besalle, R., Bisello, A., Nakamoto, C., Rosenblatt, M., Suva, L.J. & Chorev, M. (1997) Direct mapping of an agonist-binding domain within the parathyroid hormone/parathyroid hormone-related protein receptor by photoaffinity crosslinking. Proc. Natl Acad. Sci. USA 94, 3644-3649.
11. 11. Adams, A.E., Bisello, A., Chorev, M., Rosenblatt, M. & Suva, L.J. (1998) Arginine 186 in the extracellular N-terminal region of the human parathyroid hormone 1 receptor is essential for contact with position 13 of the hormone. Mol. Endocrinol. 12, 1673-1683.
12. 12. Bisello, A., Adams, A., Mierke, D., Pellegrini, M., Rosenblatt, M., Suva, L. & Chorev, M. (1998) Parathyroid hormone-receptor interactions identified directly by photocross-linking and molecular modeling studies. J. Biol. Chem. 273, 22498-22505.
13. 13. Mannstadt, M., Luck, M., Gardella, T. & Jüppner, H. (1998) Evidence for a ligand interaction site at the amino-terminus of the parathyroid hormone (PTH) PTH-related protein receptor from cross-linking and mutational studies. J. Biol. Chem. 273, 16890-16896.
14. 14. Behar, V., Bisello, A., Rosenblatt, M. & Chorev, M. (1999) Direct identification of two contact sites for parathyroid hormone (PTH) in the novel PTH-2 in the novel PTH-2 receptor using photoaffinity crosslinking. Endocrinology 140, 4251-4261.
15. 15. Dong, M., Wang, Y., Pinon, D., Hadac, E. & Miller, L. (1999) Demonstration of a direct interaction between residue 22 in the carboxyl-terminal half of secretin and the amino-terminal tail of the secretin receptor using photoaffinity labeling. J. Biol. Chem. 274, 903-909.
16. 16. Suva, L., Flannery, M., Caulfield, M., Findlay, D., Jüppner, H., Goldring, S., Rosenblatt, M. & Chorev, M. (1997) Design, synthesis and utility of novel benzophenone-containing calcitonin analogs for photoaffinity labeling the calcitonin receptor. J. Pharmacol. Exp. Ther. 283, 876-884.
17. 17. McNicoll, N., Gagnon, J., Rondeau, J.-J., De Ong, H. & Lean, A. (1996) Localization by photoaffinity labeling of natriuretic peptide receptor-A binding domain. Biochemistry 35, 12950-12956.
18. 3-ligand interface by photoaffinity cross-linking. Biochemistry 38, 3414-3420.
19. 19. Blanton, M.P., Li, Y.M., Stimson, E.R., Maggio, J.E. & Cohen, J.B. (1994) Agonist induced photoincorporation of a p-benzoylphenylalanine derivative of substance P into membrane-spanning region 2 of the torpedo nicotinic acetylcholine receptor ε subunit. Mol. Pharmacol. 46, 1048-1055.
20. 4 receptor from bovine aortic endothelium with photosensitive analogues of angiotensin IV. Biochemistry 37, 4280-4287.
21. 21. Ploug, M., Ostergaard, S., Hansen, L., Holm, A. & Dano, D. (1998) Photoaffinity labeling of the human receptor for urokinase-type plasminogen activator using a decapeptide antagonist. evidence for a composite ligand-binding site and a short interdomain separation. Biochemistry 37, 3612-3622.
22. 22. Miller, W.T. & Kaiser, E.T. (1988) Probing the peptide binding site of the cAMP-dependent protein kinase by using a peptide-based photoaffinity label. Proc. Natl Acad. Sci. USA 85, 5429-5433.
23. 23. Wang, J., Bauman, S. & Colman, R.F. (1998) Photoaffinity labeling of rat liver slutathione S-rransferase. 4-4, by glutathionyl S-[4-(succinimidyl)-benzophenone]. Biochemistry 37, 15671-15679.
24. 24. Keutmann, H.T. & Rubin, D.A. (1993) A subunit interaction site in human luteinizing hormone: identification by photoaffinity cross-linking. Endocrinology 132, 1305-1312.
25. 25. O'Neil, K.T., Erickson-Viitanen, S. & DeGrado, W.F. (1989) Photolabeling of calmodulin with basic, amphiphilic alpha-helical peptides containing p-benzoylphenylalanine. J. Biol. Chem. 264, 14571-14578.
26. 26. Rolz, C., Pellgrini, M. & Mierke, D.F. (1999) Molecular characterization of the receptor-ligand complex for parathyroid hormone. Biochemistry 38, 6397-6405.
27. B receptor. Biochemistry 38, 6043-6055.
28. 28. Breslow, R. (1980) Biomimetic control of chemical selectivity. Acc. Chem. Res. 13, 170-177.
29. 29. Scheifele, H.J. & DeTar, D.F. (1967) o-Amino-ketones of the acetophenone and benzophenone types. Org, Synth. Coll. 4, 34-38.
30. 30. DeTar, D.F. & Relya, D.I. (1954) Intramolecular reactions. II. The mechanism of the cyclization of diazotized 2-aminobenzophenones. J. Am. Chem. Soc. 76, 1680-1685.
31. 31. Simpson, J.C.E., Atkinson, C.M. & Stern, A.M. (1945) o-Amino-ketones of the acetophenone and benzophenone types. J. Chem. Soc. 646-657.
32. 32. DeTar, D.F. & Whiteley, T.E. (1957) Intramolecular reactions. V. Factors affecting the yield in diazonium cyclization reactions. J. Am. Chem. Soc. 79, 2498-2502.
33. 33. Uretskaya, G.Y. & Kraft, M.Y. (1963) Carbonyl compounds of fluorene series. I. Synthesis of 9-oxofluorene-3-carboxyaldehyde, fluorene-2-glyoxyaldehyde, 9-oxofluorene-2-glyoxylaldehyde and 7-gloyoxyloyl-9-oxofluorene-2-carboxylic acid and of some of their derivatives. Z. Obsch. Khim. 23, 3053-3056.
34. 34. Sieglitz, A. & Schatzkes, J. (1921) About the synthesis of iso-diphenone acid. Chem. Ber. 54, 2070-2071.
35. 35. Campbell, N. & Stafford, W.H. (1952) The ring-closure of derivatives of 2-aminofluorene. J. Chem. Soc. 299-306.
36. 36. Nakamoto, C., Behar, V., Chin, K.R., Adams, A.E., Suva, L.J., Rosenblatt, M. & Chorev, M. (1995) Probing the bimolecular interactions of parathyroid hormone with the human parathyroid hormone/parathyroid hormone-related protein receptor, 1. Design, synthesis and characterization of photoreactive benzophenone-containing analogs of parathyroid hormone. Biochemistry 34, 10546-10552.
37. 37. Pines, M., Adams, A.E., Stueckle, S., Bessalle, R., Rashti-Behar, V., Chorev, M., Rosenblatt, M. & Suva, L.J. (1994) Generation and characterization of human kidney cell lines stably expressing recombinant human PTH/ PTHrP receptor: lack of interaction with a C-terminal human PTH peptide. Endocrinology 135, 1713-1716.
38. 38. Roubini, E., Duong, L.T., Gibbons, S.W., Leu, C.T., Caulfield, M.P., Chorev, M. & Rosenblatt, M. (1992) Synthesis of fully active biotinylated analogues of parathyroid hormone and parathyroid hormone-related protein as tools for the characterization of parathyroid hormone receptors. Biochemistry 31, 4026-4033.
39. 39. Goldman, M.E., Chorev, M., Reagan, J.E., Nutt, R.F., Levy, J.J. & Rosenblatt, M. (1988) Evaluation of novel parathyroid hormone analogs using a bovine renal membrane receptor binding assay. Endocrinology 123, 1468-1475.
40. 40. Bisello, A., Greenberg, Z., Behar, V., Rosenblatt, M., Suva, L.J. & Chorev, M. (1996) Role of glycosylation in expression and function of the human parathyroid hormone/ parathyroid hormone-related protein receptor. Biochemistry 35, 15890-15895.
41. 41. Oda, R. (1982) Chemical reactions in the presence of phase-transfer catalysts. Hyomen 20, 280-287.
42. 42. Meng, B. & Ji, Q. (1983) Electrospray ionization for mass spectrometry of large biomolecules. Yiyao Gongye 2, 33-42.
43. 43. Kauer, J.C., Erickson-Viitanen, S., Wolfe, H.R. Jr & DeGrado, W.F. (1986) p-benzoyl-L-phenylalanine, a new photoreactive amino acid. Photolabeling of calmodulin with a synthetic calmodulin-binding peptide. J. Biol. Chem. 261, 10695-10700.
44. 44. Cox, J.A., Comte, M., Fitton, J.E. & DeGrado, W. (1985) The interaction of calmodulin with amphilic peptides. J. Biol. Chem. 260, 2527-2534.
45. 45. Wang, S.S. & Merrifield, R.B. (1969) Preparation of some new biphenylisopropyloxycarbonyl amino acids and their application to the solid phase synthesis of a tryptophan-containing heptapeptide of bovine parathyroid hormone. Int. J. Protein Res. 1, 235-244.
46. 46. Behar, V., Bisello, A., Rosenblatt, M. & Chorev, M. (1999) Direct identification of two contact sites for parathyroid hormone (PTH) in the novel PTH-2 receptor using photoaffinity cross-linking. Endocrinology 140, 4251-4261.