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Chemistry of Spin-Labeled Amino Acids and Peptides

Some New Mono- and Bifunctionalized Nitroxide Free Radicals

  • Chapter
Spin Labeling

Part of the book series: Biological Magnetic Resonance ((BIMR,volume 8))

Abstract

The ESR spectrum of the nitroxide group will be affected by constraint in an oriented electric or magnetic field if the nitroxide moiety combined with a macromolecule is placed in such an environment.

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REFERENCES

  • Adackaparayil, M., and Smith, J. H., 1977, Preparation and reactivity of a new spin label reagent, J. Org. Chem. 42:1655–1656.

    Article  CAS  Google Scholar 

  • Alcock, N. W., Golding B. T., Ioannou, P. V., and Sawyer, J. F., 1977, Preparation, crystal structure and reaction of a new spin-labeling reagent, cis-3,5-dibromo-4-oxo-2,2,6,6-tetramethyl- piperidin-l-yloxyl, Tetrahedron 33:2969–2980.

    Article  CAS  Google Scholar 

  • Aurich, H. G., 1982, Nitroxides, in The Chemistry of Functional Groups, Suppl. F.\The chemistry of amino, nitroso and nitro compounds and their derivatives, Chap. 14 (S. Patai, ed.), pp. 565–622, Interscience-Wiley, London.

    Google Scholar 

  • Azzi, A., Bragadin, M. A., Tamburro, A. M., and Santato, M., 1973, Site-directed spin labeling of mitrochondrial membrane, J. Biol. Chem. 248:2520–2526.

    Google Scholar 

  • Barratt, M. D., Dodd, G. H., and Chapman, D., 1969, A spin label for tyrosine residues, Biochim. Biophys. Acta 194:602–605.

    Google Scholar 

  • Barratt, M. D., Davies, A. P., and Evans, M. T. A., 1971, Maleimide and isomaleimide pyrrolidine- nitroxide spin labels, Eur. J. Biochem. 24:280–283.

    Article  PubMed  CAS  Google Scholar 

  • Berliner, L. J., 1974, Applications of spin labeling to structure conformation studies of enzymes, Prog. Bioorg. Chem. 3:1–80.

    Article  CAS  Google Scholar 

  • Berliner, L. J. (ed.), 1976, Spin Labeling: Theory and Applications, Vol. I, Academic Press, New York.

    Google Scholar 

  • Berliner, L. J. (ed.), 1979, Spin Labeling: Theory and Applications, Vol. II, Academic Press, New York.

    Google Scholar 

  • Berliner, L. J., 1983, The spin-label approach to labeling membrane protein sulfhydryl groups. Ann. N.Y. Acad. Sci. 414:153–161.

    Article  CAS  Google Scholar 

  • Berliner, L. J., and McConnell, H. M., 1966, A spin-labeled substrate for a-chymotrypsin, Proc. Natl. Acad. Sci. U.S.A. 55:708–712.

    Article  PubMed  CAS  Google Scholar 

  • Berliner, L. J., and McConnell, H. M., 1974, Urea denaturation of active-site spin-labeled α-chymotrypsin, Biochemistry 11:2921–2924.

    Article  Google Scholar 

  • Berliner, L. J., Grünwald, J., Hankovszky, H. O., and Hideg, K., 1982, A novel reversible thiol-specific spin label: Papaine active site labeling and inhibition, Anal. Biochem. 119:450–455.

    Article  PubMed  CAS  Google Scholar 

  • Beth, A. H., Balasubramanian, K., Wilder, R. T., Venkataramu, S. D., Robinson, B. H., Dalton, L. R., Pearson, D. E., and Park, J. H., 1981a, Structural and motional changes in glycerin- aldehyde-3-phosphate dehydrogenase upon binding to the band-3 protein of the erythrocyte membrane examined with 15N-, 2H-maleimide spin label and electron paramagnetic resonance, Proc. Natl. Acad. Sci. U.S.A. 78:4955–4959.

    Article  PubMed  CAS  Google Scholar 

  • Beth, A. H., Venketaramu, S. D., Balasubramanian, K., Dalton, L. R., Robinson, B. H., Pearson, D. E., Park, C. R., and Park, J. H., 1981b, 15N- and 2H-substituted maleimide spin labels: Improved sensitivity and resolution for biological EPR studies, Proc. Natl. Acad. Sci. U.S.A. 78:967–971.

    Article  PubMed  CAS  Google Scholar 

  • Bonnett, R. F. R., Brown, R. F. C., Clark, V. M., Sutherland, I. O., and Todd, A., 1959, Experiments toward the synthesis of Corrins. Part II. The preparation and reactions of Δ1pyrroline 1-oxides. J. Chem. Soc.: 2094–2102.

    Google Scholar 

  • Brière, R., Espie, J.-C., Ramasseul, R., Rassat, A., and Rey, P., 1979, Nitroxydes 91: ß-Cetoenolates nitroxydes, Tetrahedron Lett.: 941–944.

    Google Scholar 

  • Buchacenko, A. L., 1965, Stable Radicals, Consultants Bureau, New York.

    Google Scholar 

  • Carpino, L. A., Giza, C. A., and Carpino, B. A., 1959, O-Acylhydroxylamines. I. Synthesis of O-benzoylhydroxylamine, J. Am. Chem. Soc. 81:955–957.

    Article  CAS  Google Scholar 

  • Cazianis, C. T., Sotiroudis, T. G., and Evangelopoulos, A. E., 1980, Spin-labelling of phosphorylase b using a paramagnetic l-fluoro-2,4-dinitrobenzene derivative, Biochim. Biophys. Acta 621:117–129.

    PubMed  CAS  Google Scholar 

  • Chan, D. C. F., and Piette, L. H., 1980, ESR spin label studies of the nucleosome core particle and hystone core, Biochim. Biophys. Acta 623:32–45.

    PubMed  CAS  Google Scholar 

  • Cherry, R. J., 1979, Rotational and lateral diffusion of membrane proteins, Biochem. Biophys. Acta 559:289–327.

    PubMed  CAS  Google Scholar 

  • Crouch, R. K., Ebrey, T. G., and Govindjee, R., 1981, A bacteriorhodopsin analogue containing the retinal nitroxide free radical, J. Am. Chem. Soc. 103:7364–7366.

    Article  CAS  Google Scholar 

  • Csekö, J., Hankovszky, H. O., and Hideg, K., 1985, Synthesis of novel highly reactive l-oxyl-2,2,6,6- tetramethyl-l,2,5,6-tetrahydropyridine derivatives, Can. J. Chem. 63:940–943.

    Article  Google Scholar 

  • Dreyer, J.-L., Beinert, H., Keana, J. F. W., Hankovszky, H. O., Hideg, K., Eaton, S. S., and Eaton, G., 1983, A spin label study of the disposition of the Fe-S cluster with respect to the active center of aconitase. Biochim. Biophys. Acta 745:229–236.

    Article  PubMed  CAS  Google Scholar 

  • Dugas, H., 1977, Spin-labelled nucleic acids, Acc. Chem. Res. 10:47–54.

    Article  CAS  Google Scholar 

  • Fehér, G., 1969, Electron Paramagnetic Resonance with Applications to Selected Problems in Biology, Gordon and Breach, New York.

    Google Scholar 

  • Filatova, M. P., Reissmann, Z., Reutova, T. O., Ivanov, V. T., Grigoryan, G. L., Shapiro, A. M., and Rozantsev, E. G., 1977, Conformational states of bradykinin and its analogs in solution. III. EPR spectra of spin-labeled analogs, Bioorg. Chim. 3:1181–1189.

    CAS  Google Scholar 

  • Fittkau, S., and Damerau, W., 1980, Spinmarkierte Oligopeptide als Substratanaloge Inhibitoren der Leucinaminopeptidase, J. Prakt. Chem. 322:1032–1038.

    Article  CAS  Google Scholar 

  • Fittkau, S., Kaemmerer, G., and Damerau, W., 1979, The binding center of leucine aminopeptidase. Investigations with substrate analogs and spin-labeled inhibitors, Ophthalmic Res. 11:381–385.

    CAS  Google Scholar 

  • Flohr, K., and Kaiser, E. T., 1972, Enantiomeric specificity in the chymotrypsin-catalyzed hydrolysis of 3-carboxy-2,2,5,5-tetramethylpyrrolidin-l-oxy-p-nitrophenyl ester, J. Am. Chem. Soc. 94:3675–3676.

    Article  PubMed  CAS  Google Scholar 

  • Flohr, K., Paton, R. M., and Kaiser, E. T., 1971, Enantiomeric specificity in the cyclohexamylase- catalyzed hydrolysis of 3-carboxy-2,2,5,5-tetramethylpyrrolidin-l-oxy m-nitrophenyl ester, J. Chem. Soc.: 1621–1622.

    Google Scholar 

  • Forrester, A. R., Hay, J. M., and Thomson, R. H., 1968, Organic Chemistry of Stable Free Radicals, Academic Press, New York.

    Google Scholar 

  • Gaffney, B. J., 1976, The chemistry of spin labels, in Spin Labeling: Theory and Applications, Vol. I (L. J. Berliner, ed.), Chap. 5, pp. 183–272, Academic Press, New York.

    Google Scholar 

  • Gaffney, B. J., and McNamee, C. M., 1974, Spin label measurements in membranes, Methods Enzymol. 32:161.

    Article  PubMed  CAS  Google Scholar 

  • Gaffney, B. J., Willingham, G. L., and Schepp, R. S., 1983, Synthesis and membrane interactions of spin-label bifunctional reagents, Biochemistry 22:881–892.

    Article  PubMed  CAS  Google Scholar 

  • Gerig, J. T., Reinheimer, J. D., and Robinson, R. H., 1979, Modification of human serum albumin with N-(2,5-dinitro-4-fluorophenyl)-4-amino-2,2,6,6-tetramethylpiperidinooxy radical, Biochim. Biophys. Acta 579:409–420.

    CAS  Google Scholar 

  • Gnewuch, T., and Sosnovsky, G., 1986, Spin-labeled carbohydrates, Chem. Rev. 86:203–238. v. Goldammer, E., Kreysch, W., and Wenzel, H., 1978, Proton NMR relaxation studies of several nitroxyl-water systems, J. Solution Chem. 7:197–204.

    Google Scholar 

  • Golding, B. T., Ioannou, P. V., and O’Brien, M. M., 1975, A short-cut to spin-labelled amides, Synthesis: 462–463.

    Google Scholar 

  • Griffith, H. O., and McConnell, H. M., 1966, A nitroxide-maleimide spin label, Proc. Natl. Acad. Sci. U.S.A. 55:8–11.

    Article  PubMed  CAS  Google Scholar 

  • Griffith, O. H., and Waggoner, A. S., 1969, Nitroxide free radicals: Spin labels for probing biomolecular structure, Acc. Chem. Res. 2:17–24.

    Article  CAS  Google Scholar 

  • Griffith, O. H., Keana, J. F. W., Noall, D. L., and Ivey, J. L., 1967, Nitroxide mixed carboxylic- carbonic acid anhydrides. A new class of versatile spin labels, Biochim. Biophys. Acta 148:583–585.

    PubMed  CAS  Google Scholar 

  • Grigoryan, G. D., Rozantsev, E. G., Teplov, N. E., Ivanov, V. P., and Korkmazyan, M. M., 1973, Investigation of a-chymotripsin by the “Spin label method” at Serine-195, Izv. Akad. Nauk SSSR, Ser. Khim.: 1654–1656.

    Google Scholar 

  • Hankovszky, H. O., Hideg, K., and Tigyi, J., 1978, Nitroxides II. l-Oxyl-2,2,5,5-tetramethylpyrro- line-3-carboxylic acid derivatives, Acta Chim. Acad. Sci. Hung. 98:339–348.

    CAS  Google Scholar 

  • Hankovszky, H. O., Hideg, K., Lex, L., and Tigyi, J., 1979, Nitroxyls IV. Synthesis of spin labelled iV-(4-piperidinyl-oxycarbonyl)imidazoles and 4-piperidinyloxycarbonyl azides and their reac¬tion with amino acid derivatives, Synthesis: 530–531.

    Google Scholar 

  • Hankovszky, H. O., Hideg, K., and Lex, L., 1980, Nitroxyls VII. Synthesis and reactions of highly reactive l-oxyl-2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-ylmethyl sulfonates, Synthesis: 914–916.

    Google Scholar 

  • Hankovszky, H. O., Hideg, K., and Lex, L., 1981, Nitroxyls VIII. Synthesis of nitroxylphos- phinimines; A convenient route to Amine, Isothiocyanate, Aminocarbonylaziridine and Carbodiimide nitroxyls, Synthesis: 147–149.

    Google Scholar 

  • Hankovszky, H. O., Hideg, K., Lex, L., Kulcsár, Gy., and Halasz, A. H., 1982, Methods for preparation of heterobifunctional nitroxides: α, ß-unsaturated ketones, ß-ketoesters, cyanonitro-derivatives. Can. J. Chem. 60:1432–1438.

    Article  CAS  Google Scholar 

  • Hankovszky, H. O., Hideg, K., Goldammer, E. v., Matuszak, E., Kolkenbrock, H., Tschesche, H., and Wenzel, H., 1987, New nitroxide reagents for the selective spin labeling at the guanidino moiety of arginine residues in peptides and proteins, Biochim. Biophys. Acta 916:152–155.

    Article  CAS  Google Scholar 

  • Hideg, K., and Lex, L., 1984, A versatile new method for the synthesis of various pyrrolidin-l-oxyl fatty acids. J. Chem. Soc., Chem. Commun.: 1263–1265.

    Google Scholar 

  • Hideg, K., and Lex, L., 1986a, Synthesis of various new nitroxide free radical fatty acids. J. Chem. Soc., Perkin Trans. 1: 1431–1438.

    Google Scholar 

  • Hideg, K., and Lex, L., 1987, Synthesis of new 2-mono and 2,5-bis-functionalized pyrrolidine-1- oxyl spin labels. J. Chem. Soc., Perkin Trans. 1: 1117–1121.

    Google Scholar 

  • Hideg, K., Hankovszky, H. O., and Tigyi, J., 1977, Nitroxides I. Sulfonic esters of4-hydroxy-2,2,6,6- tetramethylpiperidine-l-oxyl and their reaction with dinucleophilic reactants, Acta Chim. Acad. Sci. Hung. 92:85–87.

    CAS  Google Scholar 

  • Hideg, K., Lex, L., Hankovszky, H. O., and Tigyi, J., 1978, Nitroxyls III. Synthesis of spin-labelled amino acids and their derivatives. Synthesis: 914–917.

    Google Scholar 

  • Hideg, K., Hankovszky, H. O., Lex, L., and Kulcsar, Gy., 1980, Nitroxyls VI. Synthesis and reactions of 3-hydroxymethyl-2,2,5,5-tetramethyl-2,5-dihydropyrrole-l-oxyl and 3-formyl derivatives, Synthesis: 911–914.

    Google Scholar 

  • Hoffman, B. M., Schofield, P., and Rich, A., 1969, Spin-labeled transfer RNA, Proc. Nat. Acad. Sci. U.S.A. 62:1195–1202.

    Article  CAS  Google Scholar 

  • Hoffman, B. M., Schofield, P., and Rich, A., 1970, Spin labeling studies of aminoacyl transfer ribonucleic acid, Biochemistry 9:2525–2532.

    Article  PubMed  Google Scholar 

  • Hsia, J. C., 1968, Development of single and double spin labelling methods and their application to study of antibody active sites, Ph.D. Thesis, University of Hawaii, Honolulu.

    Google Scholar 

  • Hsia, J. C., and Tan, C. T., 1978, Membrane immunoassay: Principle and application of spin membrane immunoassay, Ann. N.Y. Acad. Sci. 308:139–148.

    Article  CAS  Google Scholar 

  • Hsia, J. C., and Kwan, N. H., 1981, Human serum albumin: Binding specificity and allosteric effects of parinarate and stearate, A dianionic spin label study, J. Biol Chem. 256:2242–2244.

    PubMed  CAS  Google Scholar 

  • Hsia, J. C., Kosman, D. J., and Piette, L. H., 1969, Organophosphate spin-label studies of inhibited esterases, α-chymotripsin and cholinesterase, Biochem. Biophys. Res. Commun. 36:75–88.

    Article  PubMed  CAS  Google Scholar 

  • Hsia, J. C., Wong, L. T. L., and Kalow, W., 1973, Homogenous murine myeloma protein 315 and spin labeled DNP as a model system for spin labeled hapten titration. Technical and spin immunoassay, J. Immunol. Methods 3:17–24.

    CAS  Google Scholar 

  • Hsia, J. C., Er, S. S., Tan, C. T., Estes, T., and Ruoslahti, E., 1980, α-Fetoprotein binding specificity for arachidonate, bilirubin, docosa-hexanoate and palmitate; A spin label study, J. Biol. Chem. 255:4224–4227.

    PubMed  CAS  Google Scholar 

  • Hyde, J. S., and Dalton, L. R., 1979, Saturation-transfer spectroscopy, in: Spin Labeling: Theory and Applications, Vol. II (L. J. Berliner, ed.), Chap. 1, pp. 1–70, Academic Press, New York.

    Google Scholar 

  • Jahr, D., Rebhan, K. H., Schwarzhans, K. E., and Wildemann, J., 1973, Metal complexes with paramagnetic derivatives of 1-piperidine-oxyl, Z. Naturforsch. 28b:55–62.

    Google Scholar 

  • Jost, P., and Griffith, O. H., 1972, Electron spin resonance and the spin labeling method, Methods Pharmacol. 2:223–276.

    CAS  Google Scholar 

  • Jost, P. C., and Griffith, O. H., 1978, The spin labeling technique, Methods Enzymol. 49:369–418.

    Article  PubMed  CAS  Google Scholar 

  • Kalk, A., de Jong, A. S. H., and Barratt, M. D., 1975, The binding of a spin-labelled dipeptide to papain, FEBS Lett. 60:58–61.

    Article  PubMed  CAS  Google Scholar 

  • Kalmanson, A. E., and Grigoryan, G. L., 1973, Spin labels in E.P.R. investigation of biological systems, in Experimental Methods in Biophysical Chemistry(C. Nicolau, ed.), pp. 589–612, Wiley, New York.

    Google Scholar 

  • Kamzolova, S. G., and Postnikova, G. B., 1981, Spin-labeled nucleic acids, Q. Rev. Biophys. 14:223–288.

    Article  PubMed  CAS  Google Scholar 

  • Keana, J. F. W., 1978, Newer aspects of the synthesis and chemistry of nitroxide spin labels, Chem. Rev. 78:37–64.

    Article  CAS  Google Scholar 

  • Keana, J. F. W., 1979, New aspects of nitroxide chemistry, in Spin Labeling: Theory and Applications(L. J. Berliner, ed.), Chap. 3, pp. 115–172, Academic Press, New York.

    Google Scholar 

  • Keana, J. F. W., 1984, Synthesis and chemistry of nitroxide spin labels, in Spin Labeling in Pharmacology(J. L. Holtzman, ed.), Chap. 1, pp. 1–85, Academic Press, Orlando.

    Google Scholar 

  • Keana, J. F. W., Keana, S. B., and Beetham, D., 1967, A new versatile ketone spin label, J. Am. Chem. Soc. 89:3055–3056.

    Article  CAS  Google Scholar 

  • Keana, J. F. W., Lee, T. D., and Bernard, E. M., 1976, Side chain substituted 2,2,5,5-tetramethylpyr- rolidine-N-oxyl (proxyl) nitroxides. A new series of lipid spin labels showing improved properties for the study of biological membranes, J. Am. Chem. Soc. 98:3052–3053.

    Article  PubMed  CAS  Google Scholar 

  • Keana, J. F. W., Hideg, K., Birrell, B. G., Hankovszky, H. O., Ferguson, G., and Parvez, M., 1982, New mono- and difunctionalized 2,2,5,5-tetramethylpyrrolidine- and A3-pyrroline-l- oxyl nitroxide spin labels, Can. J. Chem. 60:1439–1447.

    Article  CAS  Google Scholar 

  • Keana, J. F. W., Cuomo, J., Lex, L., and Seyedrezai, S. E., 1983a, Azethoxyl nitroxide spin labeled crown ethers and cryptands with the N-0 group positioned near the cavity, J. Org. Chem. 48:2647–2654.

    Article  CAS  Google Scholar 

  • Keana, J. F. W., Seyedrezai, S. E., and Gaughan, G., 1983b, Difunctionalized trans-2,5-disub- stituted pyrrolidine (azethoxyl) nitroxide spin labels, J. Org. Chem. 48:2644–2647.

    Article  CAS  Google Scholar 

  • Keana, J. F. W., Heo, G. S., and Gaughan, G. T., 1985, Stereospecific synthesis of difunctionalized 2,5-disubstituted cis-2,5-dimethylpyrrolidine (azethoxyl) nitroxides by oxidative cleavage of protected 8-azabicyclo(3.2.1)octane precursors, J. Org. Chem. 50:2346–2351.

    Article  CAS  Google Scholar 

  • Kemp, D. S., Wang, S. W., Busby, G., and Hugel, G., 1970, Microanalysis by successive isotopic dilution. A new assay for racemic content, J. Am. Chem. Soc. 92:1043–1055.

    Article  PubMed  CAS  Google Scholar 

  • Kenyon, G. L., and Bruice, T. W., 1977, Novel sulfhydryl reagents, Methods Enzymol. 47E:407–430.

    Article  Google Scholar 

  • Klee, W., and Brenner, M., 1961, t-Butyloxycarbonyl-imidazol und t-butyl-oxycarbonyl-hydrazin, Helv. Chim. Acta 44:2141–2153.

    Article  Google Scholar 

  • Koch, T. R., Kuo, L. C., Douglas, E. G., Jaffer, S., and Makinen, M. W., 1979, Synthesis of chromophoric, spin-label enzyme substrates useful for cryoenzymology, J. Biol. Chem. 254:12310–12313.

    PubMed  CAS  Google Scholar 

  • Konieczny, M., and Sosnovsky, G., 1981, Methods for the preparation of spin labeled phosphorous compounds and applications of some of them to phosphorylative spin labeling, Synthesis: 682–699.

    Google Scholar 

  • Kumarev, V. P., and Knorre, D. G., 1970, Water-soluble carbodiimides with spin label, Dokl. Akad. NaukSSSR 193:103–105.

    CAS  Google Scholar 

  • Lawrence, J.-J., Berne, L., Ouvrier-Buffer, J. L., and Piette, L. H., 1980, Spin label study of histone Hl-DNA interaction. Comparative properties of the central part of the molecule and the amino- and carboxy-amino tails, Eur. J. Biochem. 107:263–269.

    Article  PubMed  CAS  Google Scholar 

  • Lee, T. D., and Keana, J. F. W., 1978, Nitroxides derived from 3,4-dihydro-2,5-dimethyl-2H-pyrrole 1-oxide. A new series of minimum steric perturbation lipid spin labels. J. Org. Chem. 43:4226–4231.

    CAS  Google Scholar 

  • Lee, T. D., Birrell, G. B., and Keana, J. F. W., 1979, Azetoxyl nitroxide spin labels. ESR studies involving thiourea crystals, model membrane systems and chromatophores, and chemical reduction with ascorbate and dithiothreitol. Biochim. Biophys. Acta 550:369–383.

    Article  PubMed  CAS  Google Scholar 

  • Leute, R., Ullman, E. F., Goldstein, A., and Herzenberg, L. A., 1972, Spin immunoassay technique for determination of morphine, Nature (London), New Biol. 236:93–94.

    CAS  Google Scholar 

  • Lex, L., Hideg, K., and Hankovszky, H. O., 1982, Nitroxides IX. Synthesis of nitroxide free radical a-amino acids, Can. J. Chem. 60:1448–1451.

    Article  CAS  Google Scholar 

  • Likhtenshtein, G. I., 1974, Method spinovykh metok v. molekularnoi biologii, Nauka, Moscow (in Russian); translation: Likhtenshtein, G. I., 1976, Spin Labeling Methods in Molecular Biology, Wiley-Interscience, New York.

    Google Scholar 

  • Lord, S. T., and Breslow, E., 1978, Nuclear magnetic resonance of neurophysin: Evidence for secondary peptid-binding sites, Biochem. Biophys. Res. Commun. 80:63–70.

    Article  PubMed  CAS  Google Scholar 

  • Lord, S. T., and Breslow, E., 1979, Identification and observation of alkyl proton resonances of the amino-terminal residues of bovine neurophysins. Evidence for conformational differences between neurophysin I., and neurophysin II., Int. J. Pept. Protein Res. 13:71–77.

    Article  CAS  Google Scholar 

  • Lord, S. T., and Breslow, E., 1980, Synthesis of peptide spin-labels that bind to neurophysin and their application to distance measurements within neurophysin complexes, Biochemistry 19:5593–5602.

    Article  PubMed  CAS  Google Scholar 

  • Lundt, S. L., and Breslow, E., 1976, Electron spin resonance studies of neurophysin and its interaction with spin-labeled peptides, J. Phys. Chem. 80:1123–1126.

    Article  CAS  Google Scholar 

  • Maksimova, L. A., Grigoryan, G. L., and Rozantsev, E. G., 1975, Synthesis of spin labeled peptides, Izv. Akad. Nauk SSSR, Ser. Khim.: 945–948.

    Google Scholar 

  • Marsh, D., 1981, Electron spin-resonance: Spin-labels, in Membrane Spectroscopy, Molecular Biology, Biochemistry and Biophysics, Vol. 31 (E. Grell, ed.), pp. 51–141, Springer-Verlag, Berlin, Heidelberg, New York.

    Google Scholar 

  • Marsh, D., and Watts, A., 1982, Spin labeling and lipid-protein interactions in membranes, in Lipid-Protein Interactions, Vol. 2 (P. Jost, and G. H. Griffith, eds.), pp. 53–126, Wiley, New York.

    Google Scholar 

  • McConnell, H. M., and Gafïney-McFarland, B., 1970, Physics and chemistry of spin labels, Q. Rev. Biophys. 3:91–136.

    Article  PubMed  CAS  Google Scholar 

  • McConnell, H. M., Deal, W., and Ogata, R. T., 1969, Spin labelled hemoglobin derivatives in solution, polycrystalline suspensions and single crystals, Biochemistry 8:2580–2585.

    Article  PubMed  CAS  Google Scholar 

  • Mehlhorn, R., Swanson, M., Packer, L., and Smith, P., 1980, An imidoester spin probe to membrane protein interactions: Application to cytochrome C, Arch. Biochem. Biophys. 204:471–476.

    Article  PubMed  CAS  Google Scholar 

  • Misharin, A. Yu., Vinokurov, L. M., and Polyanovskii, O. L., 1974, New paramagnetic derivative of iodoacetic acid, Izv. Akad. Nauk SSSR, Ser. Khim.: 1897–1898.

    Google Scholar 

  • Misharin, A. Yu., Azhaev, A. V., Timofeev, P. V., and Polyanovskii, O. L., 1975, Interaction of spin-labeled inhibitors with aspartate aminotransferase, Bioorg. Khim. 1:257–266.

    CAS  Google Scholar 

  • Morrisett, J. D., 1976, The use of spin labels for studying the structure and function of enzymes, in Spin Labelling: Theory and Application, Vol. I. (L. J. Berliner, ed.), pp. 273–372, Academic Press, New York.

    Google Scholar 

  • Morrisett, J. D., and Broomfield, C. A., 1972, A comparative study of spin labelled serine enzymes: Acetylcholinesterase, trypsin, a-chymotrypsin, elastase, and subtilisin, J. Biol. Chem. 247:7224–7231.

    PubMed  CAS  Google Scholar 

  • Nakaie, C. R., Goissis, G., Schreier, S., and Paiva, A. C. M., 1981, pH-dependence of EPR spectra of nitroxides containing ionizable groups, Brazilian J. Med. Biol. Res. 14:173–180.

    CAS  Google Scholar 

  • Ogawa, S., and McConnell, H. M., 1967, A spin label study of hemoglobin conformations in solution, Proc. Natl Acad. Sci. U.S.A. 58:19–26.

    Article  PubMed  CAS  Google Scholar 

  • Pirrwitz, J., and Damerau, W., 1976, Synthese spinmarkierter Alkylamine als potentielle Enzym- efïektoren, Z. Chem. 16:401–402.

    CAS  Google Scholar 

  • Price, N. C., 1973, Improvement of the spin-labeling technique by the use of a radioactive spin label, FEBS Lett. 36:351–354.

    Article  PubMed  CAS  Google Scholar 

  • Rassat, A., and Rey, P., 1967, Nitroxides, XXIII. Préparation d’aminoacides radicalaires et de leurs sels complexes. Bull. Soc. Chim. Fr.: 815–817.

    Google Scholar 

  • Rassat, A., and Ronzaud, J., 1976, Nitroxides—LXXI. Synthèse de dérivés nitroxydes du tropane. Etude par RPE et RMN des interactions hyperfines à longue distance dans ces radicaux, Tetrahedron: 239–244.

    Google Scholar 

  • Rauchman, E. J., and Rosen, G. M., 1976, Synthesis of spin labeled probes: Esterification and reduction, Synth. Commun. 6:325–329.

    Article  Google Scholar 

  • Reissmann, S., Filatova, M. P., Reutova, T. O., Arold, H., and Ivanov, V. T., 1976, Peptide XXV. Synthese von Bradykinin-Analoga und Partialsequenzen mit Tyrosin für Elektronenspin- rezonanz- und Fluoreszenzuntersuchungen, J. Prakt. Chem. 318:429–440.

    Article  CAS  Google Scholar 

  • Rozantsev, E. G., 1970, Free Nitroxyl Radicals, Plenum Press, New York. (Translated from Russian by B. J. Hazzard.).

    Google Scholar 

  • Rozantsev, E. G., and Sholle, V. D., 1971a, Synthesis and reactions of stable nitroxyl radicals, I. Synthesis, Synthesis: 190–202.

    Google Scholar 

  • Rozantsev, E. G., and Sholle, V. D., 1971b, Synthesis and reactions of stable nitroxyl radicals, II. Reactions, Synthesis: 401–414.

    Google Scholar 

  • Schlude, H., 1973, Oxidation of hydroxylamines to nitroxyl radicals with Fremy’s salt, Tetrahedron: 4007–4011.

    Google Scholar 

  • Schlude, H., 1975, New phosphonium salts for the Wittig synthesis of aldehydes from ketones. Acetal, triphenyl phosphorane, enol ether, acidic hydrolysis, nitroxyl, Tetrahedron: 89–92.

    Google Scholar 

  • Schmidt, P. G., Bertanowicz, M. S., and Rich, D. H., 1982, Spin-labeled pepstatin binding to pepsin. A study by electron spin resonance and nuclear magnetic resonance, Biochemistry 21:1830–1835.

    CAS  Google Scholar 

  • Shapiro, A. B., Pavlikov, V. V., and Rozantsev, E., 1977a, Stable radicals in diene synthesis, Dokl. Akad. Nauk SSSR 232:398–400.

    CAS  Google Scholar 

  • Shapiro, A. B., Skripnichenko, L. N., Chumakov, V. M., Pavlikov, V. V., and Rozantsev, E. G., 1977b, Interaction of paramagnetic Mannich-bases with cysteine and biopolymer molecules, Bioorg. Khim. 3:707–708.

    CAS  Google Scholar 

  • Sholle, V. D., Golubev, V. A., and Rozantsev, E. G., 1971, Interaction of nitroxyl radicals with Grignard reagents, Dokl. Akad. Nauk SSSR 200:137–139.

    CAS  Google Scholar 

  • Sinha, B. K., and Chignell, C. F., 1979, The synthesis and use of spin-labeled analogs of biotin in the study of avidin, Methods Enzymol. 62:295–308.

    Article  PubMed  CAS  Google Scholar 

  • Smith, I. C. P., 1968, A study of the conformational properties of bovine pancreatic ribonuclease A by electron paramagnetic resonance, Biochemistry 7:745–757.

    Article  PubMed  CAS  Google Scholar 

  • Smith, I. C. P., 1972, The spin label method, in Biological Applications of Electron Spin Resonance Spectroscopy(J. R. Bolton, D. Borg, and H. Schwartz, eds.), pp. 483–539, Wiley, New York.

    Google Scholar 

  • Soltys, B. J., and Hsia, J. C., 1978a, Human serum albumin, Biol Chem. 253:3029–3034.

    CAS  Google Scholar 

  • Soltys, B. J., and Hsia, J. C., 1978b, Steroid modulation of human serum albumin binding properties, J. Biol. Chem. 253:4266–4269.

    PubMed  CAS  Google Scholar 

  • Sosnovsky, G., and Konieczny, M., 1976, Phosphorylative spin-labeling of amino acids and steroids, Synthesis: 537–539.

    Google Scholar 

  • Spallholz, J. E., and Piette, L. H., 1972, Interactions of spin-labelled analogs of 1,10-phenanthroline and iodoacetamides with horse liver alcohol dehydrogenase, Arch. Biochem. Biophys. 148:596–606.

    Article  PubMed  CAS  Google Scholar 

  • Sparrow, J. T., 1976, An improved polystyrene support for solid phase peptide synthesis, J. Org. Chem. 41:1350–1353.

    Article  PubMed  CAS  Google Scholar 

  • Staab, H. A., 1977, Reactionsfähige heterocyclische Diamine der Kohlensäure, Justus Liebigs Ann. Chem. 609:75–83.

    Google Scholar 

  • Staab, H. A., and Mannschreck, A., 1962, Synthese von Carbonsäureestern nach der Imidazolid- methode, Chem. Ber. 95:1284–1297.

    Article  CAS  Google Scholar 

  • Stone, T. J., Buckmann, T., Nordio, R. L., and McConnell, H. M., 1965, Spin labeled biomolecules, Proc. Natl. Acad. Sei. U.S.A. 54:1010–1017.

    Article  CAS  Google Scholar 

  • Stryer, L., and Griffith, H. O., 1965, A spin label hapten, Proc. Natl. Acad. Sei. U.S.A. 54:1785–1791.

    Article  CAS  Google Scholar 

  • Terzian, G., Cormons, A., Asso, M., and Benlian, D., 1976, Complexes de l’acide amino-4 tétraméthyl-2,2,6,6-pipéridine oxyle-1 carboxylique-4 avec Co2+et Mn2+en solution. J. Chim. Phys. 73:146–248.

    CAS  Google Scholar 

  • Thomas, D. P., Dalton, L. R., and Hyde, J. S., 1976, Rotational diffusion studied by passage saturation transfer electron paramagnetic resonance, J. Chem. Phys. 65:3006–3024.

    Article  CAS  Google Scholar 

  • Tse-Tang, M. W., Gaffney, B. J., and Kelly, R. E., 1981, Synthesis of bifunctional spin label molecules and their orientations in membranes, Heterocycles 15:965–974.

    Article  CAS  Google Scholar 

  • Ullman, E. F., Call, L., and Osiecki, J. H., 1970, Stable free radicals. VIII. New imino, amido and carbamoyl nitroxides, J. Org. Chem. 35:3623–3631.

    Article  CAS  Google Scholar 

  • Ullman, E. F., Osiecki, J. H., Boocok, D. G. B., and Darcy, R., 1972, Studies of stable free radicals. X. Nitronyl nitroxide monoradicals and biradicals as possible small molecule spin labels, J. Am. Chem. Soc. 94:7049–7059.

    Article  CAS  Google Scholar 

  • Venkataramu, S. D., Pearson, D. E., Beth, A. H., Perkins, R. C., Park, C. R., and Park, J. H., 1979, Synthesis of perdeuterio-N-l-(l-oxyl-2,2,6,6-tetramethyl-4-peperidinyl)maleimide, a highly sensitive spin probe, J. Labelled Compd. 18:371–383.

    Google Scholar 

  • Weinkam, R. J., and Jörgensen, E. C., 1971a, Free radical analogs of histidine, J. Am. Chem. Soc. 93:7028–7033.

    Article  PubMed  CAS  Google Scholar 

  • Weinkam, R. J., and Jörgensen, E. C., 1971b, Angiotensin II analogs. VIII. The use of free radicals containing peptides to indicate the conformation of the carboxyl terminal region of angiotensin II., J. Am. Chem. Soc. 93:7033–7038.

    Article  PubMed  CAS  Google Scholar 

  • Wenzel, H. R., Becker, G., and v. Goldammer, E., 1978, Synthese eines bifunctionellen Spin-labels zur Quervernetzung von Proteinen, Chem. Ber. 111:2453–2454.

    Article  CAS  Google Scholar 

  • Wenzel, H. R., Tschesche, H., and v. Goldammer, E., 1983, Spin-labelled amino acids, peptides and proteins—Synthesis and applications, in Modern Methods in Protein Chemistry(H. Tschesche, ed.), pp. 385–408, Walter de Gruyler, Berlin.

    Google Scholar 

  • Weygand, F., and Geiger, W., 1956, N-Trifluoroacetyl-aminosäuren, IV. Mitteil: N-Trifluoroacety- lierung von Aminosäuren in wasserfreier Trifluoressigsäure, Chem. Ber. 89:647–652.

    Article  CAS  Google Scholar 

  • Weygand, F., and Freuendorfer, E., 1970, N-Trifluoracetyl-aminosäuren, XXI. Reduktive Entfernung des N-Trifluoracetyl- und N-Trichloracetylesters durch Natriumborhydrid mit Anwendungen in der Peptidchemie, Chem. Ber. 103:2437–2449.

    Article  PubMed  CAS  Google Scholar 

  • Whitesides, G. M., and Newirth, T. L., 1975, Reaction of n-butyllithium and 2,2,6,6-tetramethyl- piperidine nitroxide, J. Org. Chem. 40:3448–3450.

    Article  CAS  Google Scholar 

  • Willingham, G. L., and Gaffney, B. J., 1983, Reactions of spin-label cross-linking reagents with red blood cell protein, Biochemistry 22:892–898.

    Article  PubMed  CAS  Google Scholar 

  • Wünsch, E., 1974, Synthese von Peptiden, in Houben-Weyl, Methoden der Organischen Chemie, 4th edn. (E. Müller, ed.), Vol. XV/1,2, George Thieme Verlag, Stuttgart.

    Google Scholar 

  • Zhdanov, R. I., 1981, Paramagnetnüe modeli biologeckij aktivnükh soedidienii(Paramagnetic Models of Biologically Active Compounds), Nauka, Moscow (Russian).

    Google Scholar 

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Authors
  1. Kálmán Hideg
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  2. Olga H. Hankovszky
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Editors and Affiliations

  1. Ohio State University, Columbus, Ohio, USA

    Lawrence J. Berliner

  2. Hercules Incorporated Research Center, Wilmington, Delaware, USA

    Jacques Reuben

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Hideg, K., Hankovszky, O.H. (1989). Chemistry of Spin-Labeled Amino Acids and Peptides. In: Berliner, L.J., Reuben, J. (eds) Spin Labeling. Biological Magnetic Resonance, vol 8. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-0743-3_9

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  • DOI: https://doi.org/10.1007/978-1-4613-0743-3_9

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