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Monitoring in Solid-Phase Peptide Synthesis

  • Chapter
Book cover The Chemistry of Polypeptides

Abstract

After its invention by R. B. Merrifield (1962), solid-phase peptide synthesis has passed through a considerable evolution (Merrifield, 1969; Stewart and Young, 1969; Losse and Neubert, 1970a; Marshall and Merrifield, 1971); it evolved from the synthesis of a tetrapeptide (Merrifield, 1963) to the synthesis of a ribonuclease preparation (124 amino acid residues, AA) with 78% enzymatic activity (Gutte and Merrifield, 1971).

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References

  • Baas, J. M. A., Beyerman, H. C.. van de Graaf, B., and de Leer, E. W. B., 1971, The relative statistical distribution of peptides in stepwise synthesis, in “Peptides-1969” (E. Scoffone, ed.), p. 173, North-Holland, Amsterdam.

    Google Scholar 

  • Baba, T., Sugiyama, H., and Seto, S., 1971, Solid phase synthesis of the active center octapeptide of Candida krusei cytochrome C apoprotein, Sci. Rep. Res. Inst. Tokoku Univ. Ser. A 23: 85.

    CAS  Google Scholar 

  • Bayer, E., 1969. Neuere Ergebnisse der Peptidesynthese am Festkörper, Chem. Labor Betr. 20: 193.

    Google Scholar 

  • Bayer, E.. 1970, New results in the solid phase method for the synthesis of peptides, in “Peptides: Chemistry and Biochemistry” (B. Weinstein and S. Lande, eds.), p. 99, Marcel Dekker, New York.

    Google Scholar 

  • Bayer, E.. and Koenig, W. A., 1969, Sequence analysis of polypeptides by chromatography and mass spectrometry, J. Chromatog. Sci. 7: 95.

    CAS  Google Scholar 

  • Bayer, E., Hagenmaier, H.. Jung. G., and König, W., 1968a, Solid phase synthesis of oxytocin and apoferredoxin. in “Peptides 1968” (E. Bricas, ed.), p. 162, North-Holland, Amsterdam.

    Google Scholar 

  • Bayer, E., Eckstein, H., Hägele, K., König, W. A., Brüning, W., Hagenmaier, H., and Parr, W., 1970, Failure sequences in the solid phase synthesis of polypeptides, J. Am. Chem. Soc. 92: 1735.

    PubMed  CAS  Google Scholar 

  • Bayer, E., Hagenmaier, H., Jung, G., Parr, W., Eckstein, H., Hunziker, P., and Sievers, R. E., 1971, The problem of failure sequences in the solid phase synthesis of peptides, in “Peptides 1969” (E. Scoffone, ed.), p. 65, North-Holland, Amsterdam.

    Google Scholar 

  • Beacham. J., Dupuis. G., Finn, F. M.. Storey, H. T., Yanaihara, C., Yanaihara, N., and Hoffmann, K., 1971, Studies on polypeptides. XLIX. Fragment condensations with peptide derivatives related to the primary structure of ribonuclease T, J. Am. Chem. Soc. 93: 5526.

    Google Scholar 

  • Beyerman, H. C., 1972. Some fundamental experiments in solid-phase peptide synthesis, in “Progress in Peptide Research.” Vol. II (S. Lande, ed.), p. 25, Gordon and Breach, New York.

    Google Scholar 

  • Beyerman, H. C., and Hindriks, H., 1971, Determination of the completeness of coupling in solid phase peptide synthesis by a colour indicator, in “Peptides 1969” (E. Scoffone, ed.), p. 145, North-Holland, Amsterdam.

    Google Scholar 

  • Beyerman, H. C., Boers-Boonekamp, C. A. M., van Zoest, W. J., and van den Berg, D., 1967, Active esters and bifunctional catalysts in solid-phase peptide synthesis, in “Peptides” (H. C. Beyerman, A. van de Linde, and W. Maassen van den Brink, eds.), p. 117, North-Holland, Amsterdam.

    Google Scholar 

  • Beyerman, H. C., Hindriks, H., and de Leer, E. W. B., 1968B, Alcoholysis of Merrifield-type peptide—polymer bonds, Chem. Commun. 1968:1668. ’

    Google Scholar 

  • Beyerman, H. C., Hindriks, H., Hirt, J., and de Leer, E. W. B., 1971a, Alcoholysis of the peptide—polymer bond in solid-phase synthesis, in “Peptides 1969” (E. Scoffone, ed.), p. 87, North-Holland, Amsterdam.

    Google Scholar 

  • Beyerman, H. C., van der Kamp, P. R. M., de Leer, E. W. B., Maassen van den Brink, W., Parmentier, J. H., and Westerling, J., 1971b, Monitoring of solid-phase peptide synthesis by making use of N-(2–14C-Boc)-amino acids and determination of the peptide content with 35S-sulfuric acid, in “Proceedings of the Eleventh European Peptide Symposium, Vienna, Austria” (H. Nesvadba, ed.) (1973), p. 138, Amsterdam

    Google Scholar 

  • Beyerman, H. C., Lie, T. S.. and van Veldhuizen, C. J., 1971c, On the formation of pyroglutamylpeptides in solid-phase peptide synthesis. “Proceedings of the Eleventh European Peptide Symposium, Vienna, Austria” (H. Nesvadba, ed.) (1973), p. 162, Amsterdam.

    Google Scholar 

  • Beyerman, H. C., Hindriks, H., Hirt, J., de Leer, E. W. B., and van der Wide, A., 1972a, A synthesis of the decapeptide sequence proposed for the LH- and FSH-releasing homone, Rec. Tray. Chini. Pays-Bas 91: 1239.

    CAS  Google Scholar 

  • Bodanszky, M., and Bath, R. J., 1969. Active esters and resins in peptide synthesis: The role of steric hindrance, Chem. Commun, 1969: 1259.

    Google Scholar 

  • Bodanszky, M., and Sheehan, J. T., 1964, Active esters and resins in peptide synthesis, Chem. Ind. (Lond.) 1964: 1423.

    Google Scholar 

  • Bodanszky, M., and Sheehan, J. T., 1966, Active esters and resins in peptide synthesis, Chem. Ind. (Lond.), 1966: 1597.

    Google Scholar 

  • Brunfeldt, K., and Christensen, T., 1972, Process monitoring in solid phase peptide synthesis, amino group blocking effect of impure methylenechloride, FEES Letters 19:345. Brunfeldt, K., and Halstrem, J., 1970, Tritylation of a partially protected pentapeptide syn- thesized by the Merrifield solid-phase method, Acta Chem. Scand. 24: 3013.

    Google Scholar 

  • Brunfeldt, K., Roepstorff, P., and Thomsen, J., 1969, Process control in the solid phase peptide synthesis by titration of free amino groups, Acta Chem. Scand. 23: 2906.

    CAS  Google Scholar 

  • Brunfeldt, K., Roepstorff, P., and Thomson, J., 1971, Process control in automated peptide synthesis, in “Peptides-1969” (E. Scoffone, ed.), p. 148, North-Holland, Amsterdam. Brunfeldt, K., Christensen, T., and Villemoes, P., 1972a, Automatic monitoring of solid phase synthesis of a decapeptide, FEBS Letters 22:238.

    Google Scholar 

  • Brunfeldt, K., Bucher, D., Christensen, T., Roepstorff, P., Rubin, 1., Schou, O., and Villemoes, P. 1972b, Automated monitoring of solid phase peptide synthesis by perchloric acid titration, in “Chemistry and Biology of Peptides” (J. Meienhofer, ed.), p. 183, Ann Arbor Science, Ann Arbor.

    Google Scholar 

  • Chou, F. C.-H., Chawla, R. K., Kibler, R. F., and Shapira, R., 1971, Incomplete deblocking as a cause of failure sequence in solid phase peptide synthesis, J. Am. Chem. Soc. 93: 267.

    PubMed  CAS  Google Scholar 

  • Corley, L., Sachs, D. H., and Anfinsen, C. B., 1972, Rapid solid-phase synthesis of bradykinin, Biochem. Biophys. Res. Commun. 47: I353.

    Google Scholar 

  • Dorman, L. C., 1969, A non-destructive method for the determination of completeness of coupling reactions in solid phase peptide synthesis, Tetrahedron Letters 1969: 2319.

    Google Scholar 

  • Dorman, L. C., and Markley, L. D., 1971, Solid phase synthesis and antibacterial activity of N-terminal sequences of melittin, J. Med. Chem. 14: 5.

    PubMed  CAS  Google Scholar 

  • Dorman, L. C., Markley, L. D., and Mapes, D. A., 1971, A model system for studying solid phase peptide reactions, Anal. Biochem. 39: 492.

    PubMed  CAS  Google Scholar 

  • Dutta, A. S., and Morley, J. S., 1971, Polypeptides. Part XII. The preparation of 2-pyridyl esters and their use in peptide synthesis, J. Chem. Soc. (C) 1971: 2896.

    Google Scholar 

  • Esko, K., and Karlsson, S., 1970, Effects of Boc-amino acid adsorption with respect to yield and racemisation in the Merrifield method, Acta Chem. Scand. 24: 1415.

    CAS  Google Scholar 

  • Esko, K., Karlsson, S., and Porath, J., 1968, A method for determining free amino groups in polymers with particular reference to the Merrifield synthesis, Acta Chem. Scand. 22: 3342.

    CAS  Google Scholar 

  • Fankhauser, P., Brenner, M., Schilling, B., and Fries, P., 1971, Reaktionen an Trägerharzen: Zur quantitativen Bestimmung des Totalumsatzes, in “Proceedings of the Eleventh European Peptide Symposium, Vienna, Austria” (H. Nesbadva, ed.) (1973), p. 153.

    Google Scholar 

  • Felix, A. M., and Merrifield, R. B., 1970, Azide solid phase peptide synthesis, J. Am. Chem. Soc. 92: 1385.

    PubMed  CAS  Google Scholar 

  • Garden, J., II, and Tometsko, A. M., 1972, Fluorometric method for quantitative determination of free amine groups in peptide-containing Merrifield resins, Anal. Biochem. 46: 216.

    PubMed  CAS  Google Scholar 

  • Geiger, R., 1971. Die Syntheses physiologisch wirksamer Peptide, Angew. Chem. 83: 155.

    Google Scholar 

  • Geising, W., and Hörnle, S., 1971, Bestimmung freier Aminogruppen mittels 14C-markiertem Phenylisothiocyanat bei der Peptidsynthese in fester Phase, in “Proceedings of the Eleventh European Peptide Symposium, Vienna, Austria” (H. Nesvadba, ed.) (1973), p. 146.

    Google Scholar 

  • Gisin, B. F., 1972. The monitoring of reactions in solid-phase peptide synthesis with picric acid, Anal. Chim. Acta 58: 248.

    PubMed  CAS  Google Scholar 

  • Gisin, B. F., and Merrifield, R. B., 1972, Carboxyl-catalyzed intramolecular aminolysis. A side reaction in solid-phase peptide synthesis, J. Am. Chem. Soc. 94: 3102.

    PubMed  CAS  Google Scholar 

  • Gisin, B. F., Merrifield, R. B., and Tosteson, D. C., 1969, Solid-phase synthesis of the cyclododecadepsipeptide valinomycin, J. Am. Chem. Soc. 91: 2691.

    PubMed  CAS  Google Scholar 

  • Gut, V., and Rudinger, J.. 1968, Rate measurements in solid phase peptide synthesis, in “Peptides-1968” (E. Bricas, ed.), p. 185, North-Holland, Amsterdam

    Google Scholar 

  • Gutte, B., and Merrifield, R. B., 1969, The total synthesis of an enzyme with ribonuclease A activity, J. Am. Chem. Soc. 91: 501.

    PubMed  CAS  Google Scholar 

  • Gutte, B., and Merrifield. R. B., 1971, The synthesis of ribonuclease A, J. Biol. Chem. 246: 1922.

    PubMed  CAS  Google Scholar 

  • Hagenmaier, H., 1970, The influence of the chain length on the coupling reaction in solid phase peptide synthesis, Tetrahedron Letters 1970: 283.

    Google Scholar 

  • Hammerström, K., Lunkenheimer, W., and Zahn, H., 1970, Peptides 78, Merrifield synthesis of the insulin sequence B 1–8 using various thiol protecting groups, Makromol. Chem. 133: 41.

    Google Scholar 

  • Hancock, W. S., Prescott, D. J.. Nulty, W. L., Weintraub, J., Vagelos, P. R., and Marshall, G. R., 1971, The synthesis of a protein with acyl carrier protein activity, J. Am. Chem. Soc. 93: 1799.

    PubMed  CAS  Google Scholar 

  • Hancock, W. S., Prescott, D. J., Vagelos, P. R., and Marshall, G. R., 1973, Solvatation of the polymer matrix. Source of truncated and deletion sequences in solid phase synthesis, J. Am. Chem. Soc, 38: 774.

    CAS  Google Scholar 

  • Hindriks, H., 1972, Thesis (this laboratory), Delft, Vaste-fase peptide synthesen. Hirt, J., 1971, unpublished results (this laboratory).

    Google Scholar 

  • Hörnle, S., 1967, Synthese der Rinder-Insulin-A-Kette nach der Merrifield-Methode unter ausschliesslicher Verwendung von tert.-Butyloxycarbonyl-aminosäure-p-nitro-phenylestern, Hoppe-Seyler’s Z. Physiol. Chem. 348: 1355.

    PubMed  Google Scholar 

  • Hörnle, S., and Geising, W., 1971, Determination of free amino groups by the use of “C-labelled isothiocyanate during solid phase peptide synthesis, Hoppe-Seyler’s Z. Physiol. Chem. 352: 5.

    Google Scholar 

  • Jakubke, H. D., and Baumert, A., 1971, Vergleich einiger für die Festphasen-Peptidsynthese eingesetzten Kupplungsmethoden am Beispiel eines Modellpeptids, in “Proceedings of the Eleventh European Peptide Symposium, Vienna, Austria” (H. Nesvadba, ed.) (1973), p. 132, Amsterdam.

    Google Scholar 

  • Jollès, P., and Jollès, J., 1968, Synthèse par la methode de Merrifield d’un octapeptide faisant partie du lysozyme de blanc d’oeuf de Poule (enchaînement Cys64 Gly“), Hely. Chim. Acta 51: 980.

    Google Scholar 

  • Jorgensen, E. C., Windridge, G. C., Patton, W., and Lee, T. C., 1969, Angiotensin II analogs. I. Synthesis and biological evaluation of Gly’,G1y2,I1es-angiotensin II, Ac-Gly’,Gly2,I1e5angiotensin II, and Gly’,GIy2,Ile5,His(Bzl)6-angiotensin II, J. Med. Chem. 12: 733.

    PubMed  CAS  Google Scholar 

  • 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: 595.

    PubMed  CAS  Google Scholar 

  • Karlsson, S., Lindeberg, G., Porath, J., and Ragnarsson, U., 1970a, Removal of t-butyloxy-carbonyl groups in solid phase peptide synthesis, Acta Chem. Scand. 24: 1010.

    CAS  Google Scholar 

  • Karlsson, S., Lindeberg, G., and Ragnarsson, U., 1970b, Reactivity of p-nitrophenyl esters in solid phase peptide synthesis, Acta Chem. Scand. 24: 337.

    CAS  Google Scholar 

  • Khosla, M. C., Chaturvedi, N. C., Smeby, R. R., and Bumpus, F. M., 1968, Synthesis of 1-isoleucine-, 3-proline-and 5-alanine-angiotensins. II., Biochemistry 7: 3417.

    PubMed  CAS  Google Scholar 

  • Klostermeyer, H., 1968, Synthese von Gramicidin S mit Hilfe der Merrifield-Methode, Chem. Ber. 101: 2823.

    PubMed  CAS  Google Scholar 

  • Krumdieck, C. L., and Baugh, C. M., 1969, The solid-phase synthesis of polyglutamates of folid acid, Biochemistry 8: 1568.

    PubMed  CAS  Google Scholar 

  • Li, C. H., and Yamashiro, D., 1970, The synthesis of a protein possessing growth-promoting and lactogenic activities, J. Am. Chem. Soc. 92: 7608.

    PubMed  CAS  Google Scholar 

  • Loffet, A., 1968, personal communication.

    Google Scholar 

  • Loffet, A., and Dremier, C., 1971, A new reagent for the cleavage of the tertiary butyloxycarbonyl protecting group, Experientia 27: 1003.

    CAS  Google Scholar 

  • Losse, A., 1971, Einfluss der Harz-Struktur auf den Peptid-Bindungsschritt der Merrifield-Synthese, Tetrahedron Letters 1971: 4989.

    Google Scholar 

  • Losse, G., and Klengel, H., 1971, Synthese des Depsipeptides Valinomycin nach der Festphasenmethode, Tetrahedron 27: 1423.

    CAS  Google Scholar 

  • Losse, G., and Neubert, K.. 1970a. Peptidesynthese an hochpolymeren Verbindungen, Z. Chem. 10: 48.

    CAS  Google Scholar 

  • Losse, G., and Neubert, K., 1970b, Synthese von Gramicidin S durch neue Varianten der Festphasensynthese, Tetrahedron Letters 1970: 1267.

    Google Scholar 

  • Losse, G., and Ulbrich, R., 1971, Kontrolle des Umsatzgrades bei der Merrifield-Synthese, Z. Chem. 11: 346.

    CAS  Google Scholar 

  • Lübke, K., 1971, Solid-phase synthesis of Args-vasopressin, in “Peptides-1969” (E. Scoffone, ed.), p. 154, North-Holland, Amsterdam.

    Google Scholar 

  • Lunkenheimer, W., and Zahn, H., 1970, Peptide, LXXIX, Merrifield-Synthese symmetrischer Cystinpeptide, Justus Liebigs Ann. Chem. 740: 1.

    PubMed  CAS  Google Scholar 

  • Markley, L. D., and Dorman, L. C., 1970, A comparative study of terminating agents for the use in solid-phase peptide synthesis, Tetrahedron Letters 1970: 1787.

    Google Scholar 

  • Marshall, G. R., and Merrifield, R. B., 1971, Solid phase synthesis: The use of solid supports and insoluble reagents in peptide synthesis, in “Biochemical Aspects of Reactions on Solid Supports” (G. R. Stark, ed.), p. 111, Academic Press, New York and London.

    Google Scholar 

  • Mehlis, B., Fischer, W., and Niedrich, H., 1971, A method for the determination of conversion in the Merrifield peptide synthesis, in “Peptides-1969” (E. Scoffone, ed.), p. 146, North-Holland, Amsterdam.

    Google Scholar 

  • Merrifield, R. B., 1962, Peptide synthesis on a solid polymer, Fed. Proc., Fed. Am. Soc. Exptl. Biol. 21: 412.

    Google Scholar 

  • Merrifield, R. B., 1963, Solid phase peptide synthesis. 1. The synthesis of a tetrapeptide, J. Am. Chem. Soc. 85: 2149.

    CAS  Google Scholar 

  • Merrifield, R. B., 1964, Solid-phase peptide synthesis. III. An improved synthesis of bradykinin, Biochemistry 3: 1385.

    PubMed  CAS  Google Scholar 

  • Merrifield, R. B., 1965, Automated synthesis of peptides, Science 150: 178.

    PubMed  CAS  Google Scholar 

  • Merrifield, R. B., 1969, Solid-phase peptide synthesis, Advan. Enzymol. Rel. Areas Mol. Biol. 32: 221.

    CAS  Google Scholar 

  • Merrifield, R. B.. Stewart, J. M., and Jernberg, N., 1966, Instrument for automated synthesis of peptides, Anal. Chem. 38: 1905.

    PubMed  CAS  Google Scholar 

  • Mitchell, A. R., and Roeske, R. W., 1970, Amino acid insertion in solid-phase peptide synthesis, Error! Hyperlink reference not valid.. Chem. 35: 1171.

    CAS  Google Scholar 

  • Miura, Y., Toyama, M., and Seto, S., 1968, Solid phase synthesis of a nonapeptide of melittin, Sci. Rep. Res. Inst. Tohoku Univ. Ser. A 20: 41.

    CAS  Google Scholar 

  • Najjar, V. A., and Merrifield, R. B., 1966, Solid phase peptide synthesis. VI. The use of the o-nitrophenylsulfenyl group in the synthesis of the octapeptide bradykininylbradykinin, Biochemistry 5: 3765.

    CAS  Google Scholar 

  • Ney, K. H., and Polzhofer, K. P., 1968, Synthese von Casein-Peptiden nach der Merrifield-Methode, Tetrahedron 24: 6619.

    PubMed  CAS  Google Scholar 

  • Noda, K., Terada, S., Mitsuyasu, N., Waki, M., Kato, T., and Izumiya, N., 1970, Snake venom peptides. I. Solid phase synthesis of a hexapeptide fragment of cobrotoxin, Mem. Fac. Sci. Kyushu Unir. Ser. C 7: 189.

    CAS  Google Scholar 

  • Okuda, T., and Zahn, H.. 1969, Synthese der B-Ketten des Human- sowie des Rinderinsulins nach dem Festkörper-Verfahren von Merrifield, Makromol. Chem. 121: 87.

    CAS  Google Scholar 

  • Polzhofer, K. P., 1972. Synthese eines Labempfindlichen Pentadecapeptide aus Kuh-K-Casein, Tetrahedron 28: 855.

    CAS  Google Scholar 

  • Polzhofer, K. P., and Ney, K. H., 1970, Synthese von Casein-Peptiden nach der Merrifield-Methode, Tetrahedron 26: 3221.

    PubMed  CAS  Google Scholar 

  • Potts, J. T., Jr., Tregear, G. W.. Keutmann, H. T., Niall, H. D., Sauer, R., Deftos, L. J., Dawson, B. F., Hogan, M. L.. and Aurbach, G. D., 1971, Synthesis of a biologically active N-terminal tetratriacontapeptide of parathyroid hormone, Proc. Natl. Acad. Sci. 68: 63.

    CAS  Google Scholar 

  • Ragnarsson, U., Lindeberg, G., and Karlsson, S., 1970, Note on the use of active esters in combination with 1,2,4-triazole in solid phase peptide synthesis, Acta Chem. Scand. 24: 3079.

    PubMed  CAS  Google Scholar 

  • Ragnarsson, U., Karlsson S., and Sandberg, B., 1971, Studies on the coupling step in solid phase peptide synthesis. Some preliminary results from competition experiments, Acta Chem. Scand. 25: 1487.

    PubMed  CAS  Google Scholar 

  • Richards, F. F., Sloane, R. W.. Jr., and Haber, E., 1967. The synthesis and antigenic properties of a macromolecular peptide of defined s,..;uence bearing the dinitrophenol hapten, Biochemistry 6: 476.

    PubMed  CAS  Google Scholar 

  • Rivaille, P., Robinson. A.. Kamen, M., and Milhaud, G., 1971, Synthèse en phase solide de l’hormone de libération de l’hormone lutéotrophique (LH-RH), Heir. Chim. Acta 54: 2772.

    CAS  Google Scholar 

  • Rivier, J., Monahan, M., Vale, W., Grant, G., Amoss, M., Blackwell, R., Guillemin, R., and Burgus, R.. 1972. Solid phase peptide synthesis on a benzhydrylamine resin of LRF (luteinizing hormone releasing factor) and analogues including antagonists, Chimia 26: 300.

    CAS  Google Scholar 

  • Rothe, M., and Mazänek, J., 1972, Nebenreaktionen bei der Festphasen-Peptidesynthese als Folge der Bildung von Cyclopeptiden, Angew. Chem. 84: 290.

    Google Scholar 

  • Rudinger, J., and Gut, V., 1967, Discussion, in “Peptides” (H. C. Beyerman, A. van de Linde, and W. Maassen van den Brink, eds.), p. 89, North-Holland, Amsterdam.

    Google Scholar 

  • Sano, S., Tokunaga, R., and Kun, K. A., 1971, Solid phase method for peptide synthesis using macroreticular copolymers, Biochim. Biophys. Acta 244: 201.

    PubMed  CAS  Google Scholar 

  • Schaich, E., and Schneider, F. 1971, Experiments on the synthesis of a partial sequence of a streptococcal protease by the Merrifield method, Hopp-Seyler’s Z. Physiol. Chem. 352: 4.

    Google Scholar 

  • Shapira, R., Chou, F. C.-H., McKneally, S., Urban, E., and Kibler, R. F., 1971, Biological activity and synthesis of an encephalitogenic determinant, Science 173: 736.

    PubMed  CAS  Google Scholar 

  • Sieber, P., and Iselin, B., 1968, Peptidsynthesen unter Verwendung der 2-(p-Diphenyl)-iso-propyloxycarbonyl (Dpoc)-Aminoschutzgruppe, Hely. Chim. Acta 51: 622.

    CAS  Google Scholar 

  • Sievertsson, H., Chang, J.-K., von Klaudy, A., Bogentoft, C., Curry, B., Folkers, K., and Bowers, C., 1972, Two syntheses of the luteinizing hormone releasing hormone of the hypothalamus, J. Med. Chem. 15: 222.

    PubMed  CAS  Google Scholar 

  • Stewart, J. M., 1971, personal communication.

    Google Scholar 

  • Stewart, J. M., and Woolley, D. W., 1965, All-o-bradykinin and the problem of peptide anti-metabolites, Nature (Lond.) 206: 619.

    CAS  Google Scholar 

  • Stewart, J. M., and Young, J. D., 1969, “Solid Phase Peptide Synthesis,” Freeman, San Francisco.

    Google Scholar 

  • Takashima, H., du Vigneaud. V., and Merrifield, R. B., 1968, The synthesis of deaminooxytocin by the solid phase method, J. Am. Chem. Soc. 90: 1323.

    PubMed  CAS  Google Scholar 

  • Tregear, G. W., Niall, H. D., Potts, J. T., Jr., Leeman, S. E., and Chang, M. M., 1971, Synthesis of substance P, Nature New Biol. 232: 87.

    PubMed  CAS  Google Scholar 

  • Van Melick, J. E. W., and Wolters, E. T. M., 1972, Selective formylation of amino groups under neutral conditions, Synth. Commun. 2: 83.

    Google Scholar 

  • Weigele, M., Blount, J. F., Tengi, J. P., Czajkowski, R. C., and Leimgruber, W., 1972a, The fluorogenic ninhydrin reaction, structure of the fluorescent principle, J. A. Chem. Soc. 94: 4052.

    Google Scholar 

  • Weigele, M., DeBernardo, S. L., Tengi, J. P., and Leimgruber, W., 1972b, A novel reagent for the fluorometric assay of primary amines, J. Am. Chem. Soc. 94: 5927.

    CAS  Google Scholar 

  • Westall, F. C., and Robinson, A. B., 1970, Solvent modification in Merrifield solid-phase peptide synthesis, Error! Hyperlink reference not validChem. 35:2842.

    CAS  Google Scholar 

  • Weygand, F., and Obermeier, R., 1968, Messung des Umsatzes bei der Festkörper-Peptidsynthese mit Hilfe einer massenspektrometrischen Verdünnungsanalyse, Z. Naturforsch. B23: 1390.

    CAS  Google Scholar 

  • Wieland, T., Birr, C., and Flor, F., 1969a, Synthese von Antamanid mit der Merrifield-Technik, Justus Liebigs Ann. Chem. 727: 130.

    PubMed  CAS  Google Scholar 

  • Wissmann, H., and Geiger, R., 1970, Abtrennung von Fehlsequenzen in der Festphasen-Peptidsynthese mit dem Anhydrid der 3-Sulfopropionsäure, Angew. Chem. 82: 937.

    Google Scholar 

  • Wünsch, E., 1971, Synthese von Peptid-Naturstoffen, Angew. Chem. 83: 773.

    Google Scholar 

  • Yamashiro, D., Blake, J.. and Li, C. H., 1972, The use of N°,N’0“-bis(tert-butyloxycarbonyl)histidine and N°-2-(p-biphenylyl)isopropyloxycarbonyl-N”“-tert-butyloxycarbonylhistidine in the solid-phase synthesis of histidine-containing peptides, J. Am. Chem. Soc. 94: 2855.

    PubMed  CAS  Google Scholar 

  • Zhukova, G. F., Ravdel’, G. A.. and Shchukina, L. A., 1970, Synthesis of eledoisin analogs on a polymer, J. Gen. Chem. (U.S.S.R.) 40: 2750.

    Google Scholar 

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  1. Laboratory of Organic Chemistry, Technische Hogeschool, Delft, The Netherlands

    J. Hirt, E. W. B. de Leer & H. C. Beyerman

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  2. E. W. B. de Leer
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  3. H. C. Beyerman
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Editors and Affiliations

  1. Department of Biochemistry, Mount Sinai School of Medicine, City University of New York, New York, New York, USA

    P. G. Katsoyannis (Chairman) (Chairman)

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© 1973 Plenum Press, New York

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Hirt, J., de Leer, E.W.B., Beyerman, H.C. (1973). Monitoring in Solid-Phase Peptide Synthesis. In: Katsoyannis, P.G. (eds) The Chemistry of Polypeptides. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-4571-8_17

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  • DOI: https://doi.org/10.1007/978-1-4613-4571-8_17

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-4573-2

  • Online ISBN: 978-1-4613-4571-8

  • eBook Packages: Springer Book Archive

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