Protected peptide fragments

Wang SS. p-Alkoxybenzyl alcohol resin and p-alkoxybenzyloxycarbonylhy-drazide resin for solid-phase synthesis of protected peptide fragments. J Am Chem Soc 1973 95 1328-1333. 

Rink H. Solid-phase synthesis of protected peptide fragments using a trialkoxy diphenyl methylester resin. Tetrahedron Lett 1987 28 3787-3790. 

A series of polystyrene-bound substituted benzophenone oximes 71a-d have been synthesized and tested by DeGrado and Kaiser as potential supports for the solid-phase preparation of protected peptide fragments (Scheme 38). ... 

Rink, H. Solid-Phase Synthesis of Protected Peptide Fragments Using a Trialkoxydiphenyl-Methylester Resin, Tetrahedron Lett. 1987, 28, 3787-3790. 

Wang, S.-S. p-Alkoxybenzyl Alcohol Resin and p-Alkoxybenzyloxycar-bonylhydrazide Resin for Solid Phase Synthesis of Protected Peptide Fragments, J. Am. Chem. Soc. 1973, 95, 1328-1333. 

Mergler, M. Nyfeler, R. Tanner, R. Gosteli, J. Grogg, P. Peptide Synthesis by a Combination of Solid-Phase and Solution Methods. 11. Synthesis of Fully Protected Peptide Fragments on 2-Methoxy-4-alkoxybenzyl Alcohol Resin, Tetrahedron Lett. 1988, 29,4009. 

Dialkoxy- and trialkoxybenzyl esters are even more acid-labile than the Wang linker, and can, for example, be cleaved with dilute TFA, acetic acid, or hexafluoroiso-propanol without simultaneous acidolysis of Boc groups. These linkers thus enable the solid-phase synthesis of protected peptide fragments or other acid-sensitive products [33]. 

Synthesis of the peptide Ac-A-Bn-C-OH was performed by a stepwise solid-phase fragment condensation approach, as shown in Scheme 3, using the general procedures of the automated solid-phase method. The synthesis began with Boc-C-resin support and continued with the stepwise addition of protected peptide fragments until the completed peptide was assembled on the resin. The supported peptide Ac-A-Bn-C-resin was obtained after deprotection of Boc-A-Bn-C-resin and acetylation of the free amino groups. 

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-aIkoxy-benzyl alcohol resin, Tetrahedron Lett. 29, 4009—4012. 

DeGrado, W. E. and Kaiser, E. T. (1980) Polymer-bound oxime esters as supports for solid-phase peptide synthesis. The preparation of protected peptide fragments. /. Org. Chem. 45, 1295-1300. 

Blankemeyer-Menge, B. and Frank, R. (1988) Simultaneous multiple synthesis of protected peptide fragments on ally -functionalized cellulose disc supports. Tetrahedron Lett. 29, 5871-5874. 

Fig. l The use of the 2-chlorotrityl chloride resin for the preparation of protected peptides and proteins. Either amino acids (a) or fully protected peptide fragments (b) are condensed to the growing peptide chain on the resin. 

Scheme 9 Synthetic Route to a Protected Peptide Fragment of Sequence 19-23 of...

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