Abstract
Development of appropriate resin linker combinations for solid-phase peptide synthesis (SPPS) has allowed rapid access to (fully) protected peptide fragments with a free C-teminal carboxyl moiety. These fragments may be assembled either in solution or on resin—an approach that has some intrinsic advantages compared to the stepwise methodology (see Chapter 15). Approaches to synthesize such fragments usually employ “orthogonal” (see Note 1) Nα-protection/side-chain protection. The orthogonal combination Fmoc/tBu can, however, only be used if the peptide resin bond is cleavable either by acids weak enough to leave tBu groups intact or by a method employing neither acids nor bases, such as photolysis (1) or catalysis by a Pd(0) complex (2).
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References
Lloyd-Williams, P., Gairi, M., Albericio, F., and Giralt, E. (1991) Convergent SPPS X. Synthesis and purification of protected peptide fragments using the photolabile Nbb-resin. Tetrahedron 47, 9867–9880.
Kunz, H. and Dombo, B. (1988) Solild phase synthesis of peptides and glycopeptides on polymeric supports with allylic anchor groups. Angew. Chem. (Int. Engl. Ed.) 27, 711–713 (Angew. Chem. 100,732-734).
Kunz, H. and Dombo, B. (1988) Solild phase synthesis of peptides and glycopeptides on polymeric supports with allylic anchor groups. Angew. Chem. (Int. Engl. Ed.) 27, 711-713 (Angew. Chem. 100,732–734).
Rink, H. (1987) Solid phase synthesis of protected peptide fragments using a trialkoxydiphenyl-methylester resin. Tetrahedron Lett. 28,3787–3790.
Barlos, K., Gatos, D., Kallitsis, J., Papaphotiu, G., Sotiriu, P., Wenqing, Y., and Schafer, W. (1989) Darstellung geschützter Peptidfragmente unter Einsatz substituierter Triphenylmethylharze. Tetrahedron Lett. 30, 3943–3946.
Albericio, F. and Barany, G. (1991) Hypersensitive acid-labile (HAL) tris(alkoxybenzyl) ester anchoring for solid-phase synthesis of protected peptide segments. Tetrahedron Lett. 32,1015–1018.
Sheppard, R. C. and Williams, B. J. (1982) A new protecting group combination for solid phase synthesis of protected peptides. J. Chem Soc., Chem Commun., 587–589.
Florsheimer, A. and Riniker, B. (1991) Solid phase synthesis of peptides with the highly sensitive HMPB-linker (4-(4-hydroxymethyl-3-methoxy phenoxy) butyric acid). Peptides 1990, Proc 21 st EPS, Platja d’ Aro, Escom, Leiden, pp. 131–133.
Mergler, M., Nyfeler, R., Tanner, R., Gosteli, J., and Grogg, P. (1988) Peptide synthesis by a combination of solid-phase and solution methods II. Synthesis of fully protected peptide fragments on 2-methoxy-4-alkoxy-4-alkoxybenzyl alcohol resin. Tetrahedron Lett. 29,4009–4012.
Kapumiotu, A., Ungermann, C., and Voelter, W. (1992) Optimized SPPS of the new stem cell prolifering inhibiting factor Ac-SDKP and derivation. Proc. 2 nd Int. Symp. on Innovation and Perspectives in Solid Phase Synthesis, Canterbury 1991, Intercept, Andover, pp. 319–323.
Mergler, M. and Nyfeler, R. (1992) Easy synthesis ofprotected peptide hydrazides on solid support. Peptides, Chemistry and Biology Proc. 12 th APS, Boston 1991, Escom, Leiden, pp. 551–552.
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, 595–598.
Hancock, W. S. and Battersby, J. E. (1976) A new method for the detection of incomplete coupling reaction in solid phase peptide synthesis using 2,4,6-trinitrobenzenesulfonic acid. Analyt. Biochem. 71,260–263.
Riniker, B., Fretz, H., and Kamber, B. (1993) Peptides 1992 Proc. 22 nd EPS, Interlaken, Escom, Leiden, pp. 34,35.
Riniker, B., Fretz, H., and Kamber, B. (1993) Peptides 1992 Proc. 22 nd EPS, Interlaken, Escom, Leiden, pp. 34,35.
Barany, G. and Merrifield, R. B. (1979) Solid-Phase Peptide Synthesis. The Peptides, vol. 2, Academic, New York, pp. 1–284.
Athertone, E., Pinori, M., and Sheppard, R. C. (1985) Peptide synthesis 6. Protection of the sulfhydryl group of cysteine in solid-phase synthesis using N α-Fluorenylmethoxycarbonyl amino acids. Linear oxytocin derivatives. J. Chem. Soc., Perkin Trans. I,2057–2064.
White, P. (1992) Fmoc-Trp (Boc)-OH: a new derivative for the synthesis of peptides containing tryptophan. Peptides, Chemistry and Biology, Proc. 12 th APS. Boston 1991, Escom, Leiden, pp. 537–538.
Knorr, R., Trzeciak, A., Bannwarth, W., and Gillesen, D. (1989) New coupling reagents in peptide chemistry. Tetrahedron Lett. 30, 1927–1930.
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© 1994 Humana Press Inc.
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Mergler, M. (1994). Synthesis of Fully Protected Peptide Fragments. In: Pennington, M.W., Dunn, B.M. (eds) Peptide Synthesis Protocols. Methods in Molecular Biology, vol 35. Humana Press, Totowa, NJ. https://doi.org/10.1385/0-89603-273-6:287
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DOI: https://doi.org/10.1385/0-89603-273-6:287
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