Use of chlorinated benzyloxycarbonyl protecting groups to eliminate N. epsilon.-branching at lysine during solid-phase peptide synthesis

BW Erickson, RB Merrifield

Index: Erickson,B.W.; Merrifield,R.B. Journal of the American Chemical Society, 1973 , vol. 95, p. 3757 - 3763

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Citation Number: 84

Abstract

Abstract: Six ring-chlorinated derivatives of Ne-benzyloxycarbonyl-L-lysine were synthesized and their apparent first-order rates of deprotection in 50: 50 (v/v) trifluoroacetic acid-dichloromethane at 20" were quantitatively determined by ion-exchange chromatography. sec-9 follow in order of increasing stability: W-benzyloxycarbonyl-L-lysine (396)< Ne-(4-chlorobenzyloxycarbonyl)-~-lysine (1 38)<< W-(2-chlorobenzyloxycarbonyl)- ...