Merrifield solid-phase peptide synthesis

The polymeric resin used for Merrifield solid-phase peptide synthesis (Section 26.8) is prepared by treating polystyrene with iV-(hydroxymethyl) phthalimide and trifluoromethanesulfonic acid, followed by reaction with hydrazine. Propose a mechanism for both steps. 

RB Merrifield. Solid-phase peptide synthesis. Endeavour 3, 1965. 

G Barany, RB Merrifield. Solid-phase peptide synthesis, in The Peptides Analysis, Synthesis, Biology, Vol. 2, pp 1-284. Academic Press, New York, 1979. 

NMR approach for studying Merrifield solid-phase peptide synthesis, let. Lett., 1980, 21, 1397-1400. 

A. G. Ludwick, L. W. Jelinski, D. Live, A. Kintanar and J. J. Dumais, Association of peptide chains during merrifield solid-phase peptide synthesis, a deuterium NMR study, J. Am. Chem. Soc., 1986, 108, 6493-6496. 

Now we consider an example to illustrate how these procedures are combined in the Merrifield solid-phase peptide synthesis. 

Westall, E. C. and Robinson, A. B. (1970) Solvent modification in Merrifield solid-phase peptide synthesis. J. Org. Chem. 35, 2842-2844. 

R. B. Merrifield, Solid phase peptide synthesis. I. The synthesis of a tetrapeptide, J. Am. Chem. Soc. 55 2149 (1963) for recent reviews see (a) H. Benz, The role of solid-phase fragment condensation (SPFC) in peptide synthesis. Synthesis p. 337 (1994) (b) P. Lloyd-Williams, F. Alberico, and E. Giralt, Convergent solid phase peptide synthesis. Tetrahedron 49 11065 (1993). 

SL Manatt, SF Amsden, CA Bettison, WT Frazer, JT Gudman, BE Lenk, JF Lubetich, EA McNelly, SC Smith, DJ Templeton, RP Pinnell. A fluorine-19 NMR approach for studying Merrifield solid-phase peptide synthesis. Tetrahedron Lett 21 1397-1400, 1980. 

R.B. Merrifield, Solid phase peptide synthesis. The synthesis of a tetrapeplide, J. Amer. Chem. Soc., 85 (1963) 2149. 

Peptide benzyl esters can be transesterified at room temperature with methanol or ethanol in the presence of a strong anion-exchange resin (Bio-Rad AG1-X8, OH" form). The reaction is convenient for the cleavage of peptides from the resin support in the Merrifield solid-phase peptide synthesis.3 ... 

Other references related to the Merrifield solid-phase peptide synthesis are cited in the literature. ... 

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