α-(Phenylacetamido)benzylpolystyrene (pab-resin)

Autor: Giralt, E., Andreu, D., Pons, M., Pedroso, E.
Zdroj: Tetrahedron; January 1981, Vol. 37 Issue: 10 p2007-2010, 4p
Abstrakt: Solid phase peptide synthesis carried out on conventional chloromethyl polystyrene support has the disadvantage of the acidolysis of the peptide-resin linkage during the deprotection step. In addition, when trifluoroacetic acid is used as deprotecting agent, intrapolymeric trifluoroacetyl transfer may give rise to truncated trifluoroacetylated peptides. A new polymer support devised to minimize these problems, α - (4 - chloromethyl-phenylacetamido) benzylcopoly(styrene-1%-divinylbenzene) (ClCH2-Pab-resin), has been synthesized. The acetamido bridge between the peptide and the resin increases the acid stability of the new support thus allowing the synthesis of purer peptides in higher yields. Boc-aminoacyl-OCH2-Pab-resins can be readily prepared in a versatile way by reaction of Boc-amino acid caesium salts with chloromethyl-Pab-resin. This fact contrasts with the rather elaborate procedures required for previously described similar resins.
Databáze: Supplemental Index