Abstract
The minireview summarizes the recent preparation of thefollowing unusually modified combinatorial peptide collectionsuseful for diagnostics and screening in drug finding. Tissuetransglutaminase catalyzes cross couplings with transamidationbetween Gln and Lys peptide chains resulting in libraries withisopeptide bonds. The enzyme is involved in the triggering ofautoantigenic B- and T-cell epitopes of coeliac disease. Themicrobial enzyme EpiD involved in lantibiotic biosynthesiscatalyzes oxidative decarboxylation of C-terminal cysteineresidues in peptide libraries transforming peptidyl-cysteinesto peptide (2-mercaptovinyl)amides. Novel backbone modifiedpeptide libraries are prepared using oxazole and thiazolebuilding blocks carrying amino acid side chains. These aminoacids have been found in many biologically active naturalproducts from marine and microbial organisms such as microcinB17. Dityrosine and isodityrosine linked peptide dimerlibraries are accessible by oxidative phenol coupling usinghorseradish peroxidase. Such structural elements are found forexample in the polycyclic glycopeptide antibiotics of thevancomycin type. Microstructured layers of linear and cyclicpeptide libraries are generated on transducer surfaces forcellular assays, sensor developments and even chiralrecognition. Examples include a light-directed andmicrostructured electrochemical polymerization of phenollabelled peptides.
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References
Jung, G. (Ed.) Combinatorial Peptide and Nonpeptide Libraries, Wiley-VCH, Weinheim 1996, pp. 1–18.
Wiesmüller, K.-H, Fleckenstein, B. and Jung, G., Biol. Chem., 382 (2001) 571–579.
Mühlradt, P.F., Kieß , M., Meyer, H. Süß muth, R. and Jung, G., J. Exp. Med., 185 (1997) 1951–1958.
Jung, G. (Ed.), in T. Shioiri (Ed.), Peptide Science 2000, The Japanese Peptide Society, Protein Research Foundation, Osaka, Japan, 2001, pp. 1–4.
Schmid, D.G., v.d. Mülbe, F., Fleckenstein, B., Weinschenk, T. and Jung, G., Anal. Chem., 73 (2001) 6008–6013.
Jung, G., Fleckenstein, B., von der Mülbe, F., Wesels, J., Niethammer, D. and Wiesmüller, K.-H., Biologicals, 29 (2001) 179–181.
Fleckenstein, B., Jung, G. and Wiesmüller; K.-H., Seminars in Immunology, 11 (1999) 405–416.
Hin, S., Zabel, C., Bianco, A., Jung, G. and Walden, P., J. Immunol., 163 (1999) 2363–2367.
Hin, S., Bianco, A., Zabel, C., Jung, G. and Walden, P., J. Biol. Chem., 276 (2001) 48790–48796.
Jung, G. and Sahl, H.-G. (Eds.), Nisin und Novel Lantibiotics, Escom, Leiden (1991).
Jung, G., Angew. Chem. Int. Ed. Engl., 30 (1991) 1051–1068.
Jack, R.W. and Jung, G., Curr. Opinion Chem. Biol., 4 (2000) 310–317.
Schnell, N., Entian, K.-D., Schneider, U., Götz, F., Zähner, H., Kellner, R. and Jung, G., Nature, 333 (1988) 276–278.
Sahl, H.-G., Reis, M., Eschbach, M., Szekat, C., Beck-Sickinger, A., Metzger, J., Stevanovic, S. and Jung, G., In: Jung, G. and Sahl, H.-G. (Eds.) Nisin and Novel Lantibiotics, pp. 332–346, Escom, Leiden (1991).
Kupke, T., Kempter, C., Jung, G. and Götz, F., J. Biol. Chem., 270 (1995) 11282–11289.
Kempter, C., Kupke, T., Kaiser, D., Metzger, J.W. and G. Jung, G., Angew. Chem. Int. Ed. Engl., 35 (1996) 2104–2107.
Götz, F. and Jung, G. in: V. Braun, F. Götz (Eds.), Microbial Fundamentals in Biotechnology, Final report of collaborate research centre 323 (1986-1999), DFG, pp. 52–92. Wiley-VCH, Weinheim, 2001.
Kupke, T., Uebele, M., Schmid, D., Jung, G., Blaesse and M., Steinbacher, S., J. Biol. Chem., 275 (2000) 31838–31846.
Bayer, A., Freund, S. and Jung, G., Eur. J. Biochem., 234 (1995) 414–426.
Kelleher, N.L., Hendrickson, C.L. and Walsh, C.T., Biochemistry, 38 (1999) 15623–15630.
Videnov, G., Kaiser, D., Kempter, C., Brooks, M. and Jung, G., Angew. Chem. Int. Ed. Engl., 35 (1996) 1506–1508.
Kaiser, D., Videnov, G., Maichle-Moessmer, C., Strähle, J. and Jung, G., J. Chem. Soc., Perkin Trans 2 (2000) 1081–1085.
Carnio, M.C., Höltzel, A., Rudolf, M., Henle, T., Jung, G. and Scherer, S., Appl. Env. Microbiol., 66 (2000) 2378–2384.
Eickhoff, H., Rieker, A. and Jung, G., Tetrahedron, 57 (2001) 353–364.
Bischoff, D., Pelzer, S., Bister, B., Nicholson, G.J., Stockert, S., Schirle, M., Wohlleben, W., Jung, G. and Süssmuth, R. D., Angew. Chem. Int. Ed. Engl., 40 (2001) 4688–4691.
Bischoff, D., Pelzer, S., Hoeltzel, A., Nicholson, G., Stockert, S., Wohlleben, W., Jung, G. and Süß muth, R.D., Angew. Chem. Int. Ed. Engl., 40 (2001) 1693–1696.
Süß muth, R., Pelzer, S., Nicholson, G., Walk, T., Wohlleben, W.and Jung, G., Angew. Chem. Int. Ed. Engl., 38 (1999) 1976–1979.
Schmid, D.G., Hoeltzel, A., Nicholson, G.J., Stevanovic, S., Schimana, J., Gebhardt, K., Müller, J., Fiedler, H.-P. and Jung, G., in: Lebl, M., Houghten, R.A. (Eds.), Peptides: The Wave of the Future, Kluwer, Dordrecht, 2001. pp. 768–769.
Leipert, D., Heiduschka, P., Mack, J., Egelhaaf, H.J., Oelkrug, D.and Jung, G., Angew. Chem. Int. Ed. Engl., 37 (1998) 2337–2340.
Leipert, D., Mack, J., Tünnemann, R. and Jung, G. (1999) in: G. Jung (Ed.), Combinatorial Chemistry - Synthesis, Analysis, Screening, Wiley-VCH, Weinheim, 1999, pp. 335–354.
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Jung, G. Smart peptide libraries are accessible via enzymatic modifications. Letters in Peptide Science 8, 259–265 (2001). https://doi.org/10.1023/A:1016225030494
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DOI: https://doi.org/10.1023/A:1016225030494