Abstract
Peptidomimetics have become immensely important for both organic and medicinal chemists (1). The alteration of peptides to peptidomimetics has included peptide side chain manipulations, amino acid extensions (2), deletions (3), substitutions (1a,b), and most recently backbone modifications (4). It is this latter development that has been exploited for the synthesis of biomimetic polymeric structures. Such progress has been fueled by the suggestion that peptidomimetics may provide novel scaffolds for the generation of macromolecules with new properties of both biological and chemical interest (4).
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References
Spatola, A. F. (1983) Peptide backbone modifications: a structure-activity analysis of peptides containing amide bond surrogates, in Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins (Weinstein, B., ed.), Marcel Dekker, New York, pp. 267ā357.
Sherman, D. B. and Spatola, A. F. (1990) Compatibility of thioamides with reverse turn features: synthesis and conformatioinal analysis of two model cyclic pseudopeptides containing thioamides as backbone modifications. J. Am.Chem. Soc. 112, 433ā41.
Hirschmann, R. (1990) Medicinal chemistry in the golden age of biology: lessons from steroid and peptide research. Angew. Chem. Int. Ed. Engl. 29, 1278ā1301.
Gante, J. (1994) Peptidomimetics-tailored enzyme-inhibitors. Angew. Chem. Int. Ed. Engl. 33, 1699ā1720.
Freidinger, R. M., Veber, D. F., Perlow, D. S., Brooks, J. R., and Saperstein, R. (1980) Bioactive conformation of luteinizing hormone-releasing hormone: evidence from a conformationally constrained analog. Science 210, 656ā658.
Stachowiak, K., Khosla, M. C, Plucinska, K., Khairallah, P. A., and Bumpus, F. M. (1979) Synthesis of angiotensin II analogues by incorporating Ī²-homoisoleucine residues. J. Med. Chem. 22, 1128ā1132.
Sarantakis, D., McKinley, W., and Jaunakais, I. (1976) Structure activity studies on somatostatin. Clin. Endocrinol. 5, 275Sā276S.
Hagihara, M, Anthony, N. J., Stout, T. J., Clardy, J., and Schreiber, S. J. (1992) Vinylogous polypeptides: an alternative peptide backbone. J. Am. Chem. Soc. 114, 6568ā6570.
Simon, R. J., Kania, R. S., Zuckerman, R. N., Huebner, V. D., Jewell, D. A., Banville, S., Ng, S., Wang, L., Rosenberg, S., Marlowe, C. K., Spellmeyer, D. C, Tan, R., Frankel, A. D., Santi, D. V., Cohen, F. E., and Bartlett, P. A. (1992) Peptoids: a modular approach to drug discovery. Proc. Natl. Acad. Sci. USA 89, 9367ā9371.
Smith, A. B., III, Keenan, T. P., Holcomb, R. C., Sprengeler, P. A., Guzman, M. C., Wood, J. L., Carroll, P. J., and Hirschmann, R. (1992) Design, synthesis, and crystal structure of a pyrrolinone-based peptidomimetic possesing the conformation of a Ī²-strand: potential application to the design of novel inhibitors of proteolytic enzymes. J. Am. Chem. Soc. 114, 10,672ā10,674.
Cho, C. Y., Moran, E. J., Cherry, S. R., Stephans, J. C., Fodor, S. P. A., Adams, C. L., Sundaaram, A., Jacobs, J. W., and Schultz, P. G. (1993) An unnatural biopolymer. Science 261, 1303ā1305.
Liskamp, R. M. J. (1994) Opportunities for new chemical libraries: unnatural biopolymers and diversomers. Angew. Chem. Int. Ed. Engl. 33, 633ā636.
Burgess, K., Linthicum, D. S., and Shin, H. (1995) Solid-phase syntheses of unnatural biopolymers containing repeating urea units. Angew. Chem. Int. Ed. Engl. 34, 907ā909.
Han, H. and Janda, K. D. (1996) Azatides: solution and liquid phase syntheses of a new peptidomimetic. J. Am. Chem. Soc. 119, 2539ā2544.
Dutta, A. S., and Morley, J. S. (1975) Polypeptides. Part XIII. Preparation of Ī±-aza-aminoacid (cabazic acid) derivatives and intermediates for the preparation of Ī±-aza-peptides. J. Chem. Soc. Perkin Trans. 1, 1712.
Biel, J. H., Drukker, A. E., Mitchell, T. F., Sprengeler, E. P., Nuhfer, P. A., Conway, A. C, and Horita, A. (1959) Central stimulants. Chemistry and structure-activity relationships of aralkyl hydrazines. J. Am. Chem. Soc. 81, 2805ā2813.
Efimov, V. A., Kalinkina, A. L., and Chakhmakhcheva, O. G. (1993) Dipentafluorophenyl carbonate-a reagent for the synthesis of oligonucleotides and their conjugates. Nucleic Acids Res. 21, 5337ā5344.
Magrath, J. and Abeles, R. H. (1992) Cysteine protease inhibition by azapeptide esters. J. Med. Chem. 35, 4279ā4283.
Still, W.C., Kahn, M., and Mitra, A. (1978) Rapid chromatographic technique for preparative separation with modern resolution. J. Org. Chem. 43, 2923ā2925.
Geckeler, K. E. (1995) Soluble polymer supports for liquid-phase synthesis, in Advances in Polymer Science, vol. 121 (Abe, A., et al., ed.), Springer-Verlag, Berlin, p. 31.
Han, H., Wolfe, M. M., Brenner, S., and Janda, K. D. (1995) Liquid-phase combinatorial synthesis. Proc. Natl. Acad. Sci. USA 92, 6419ā6423.
Meo, T., Gansch, C, Inan, R., Hollt, V., Weber, E., Herz, A., and Riethmuller, G. (1983) Monoclonal antibody to the message sequence Tyr-Gly-Gly-Phe of opioid peptides exhibits the specificity requirements of mammalian opioid receptors. Proc. Natl. Acad. Sci. USA 80, 4084ā4089.
Kaiser, E., Colescott, R. L., Bossinger, C. D., and Cook, P. I. (1970) Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 34, 595ā598.
Hunt D. F., Yates III, J. R., Shabanowitz, J., Winston, S., and Hauser, C. R. (1986) Protein sequencing by tandem mass spectrmetry. Proc. Natl. Acad. Sci. USA 83, 6233ā6237.
Garner, B., Nakanishi, H., and Kahn, M. (1993) Conformational constrained nonpeptide Ī²-turn mimetics of enkephalin. Tetrahedron 49, 3433ā3448.
Lowe, G. H. and Bart, S. K. (1978) Energy conformation study of met-enkephalin and its D-Ala analogue and their resemblance to rigid opiates. Proc. Natl. Acad. Sci. USA 75, 7ā11.
Manavalan, P. and Momany, F. A. (1981) Conformational energy calculations on enkephalins and enkephalin analogs. Classification of conformations to different configurational types. Int. J. Pept. Protein Res. 18, 256ā275.
Smith, G. D., and Griffin, J. F. (1978) Conformation of [Leua] Enkephalin from X-ray diffraction: features important for recognition at opiate receptor. Science 199, 1214ā1216.
Ishida, T., Kenmotsu, M., Mino, Y., Inoue, M., Fujiwara, T., Tomita, K., Kimura, T., and Sakakibara, S. (1984) X-ray diffraction studies of enkephalins. Biochem. J. 218, 677ā689.
Olivato, P. R. and Guerrero, S. A. (1983) Conformational studies of Ī±-substituted carbonyl compounds. Part 1. Conformation and electronic interaction in hetero-substituted acetones by infrared and ultraviolet spectroscopy. J. Chem. Soc, Perkin Trans. II, 1053ā1058.
Graybill, T. L., Ross, J. T., Gauvin, B. R., Gregory, J. S., Harris, A. L., Ator, M. A., Rinker, J. M., and Dolle, R. E. (1992) Structure-activity relationships of the pyridazinone series of 5-lipoxygenase inhibitors. Bioorganic Med. Chem. Lett. 2, 1357ā1360.
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Han, H., Yoon, J., Janda, K.D. (1999). Azatides as Peptidomimetics: Solution and Liquid Phase Syntheses . In: Kazmierski, W.M. (eds) Peptidomimetics Protocols. Methods in Molecular Medicineā¢, vol 23. Humana Press. https://doi.org/10.1385/0-89603-517-4:87
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DOI: https://doi.org/10.1385/0-89603-517-4:87
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