Some of the peptide chains esterified to the hydroxymethyl-poly(styrene-co-divinylbenzene) resin are lost by acidolysis during solid-phase peptide synthesis. This loss has been minimized by using 4-(hydroxymethyl)phenylacetamidomethylpoly(styrene-co-divinylbenzene) as the solid support. The phenylacetamidomethyl (Pam) bridge between the peptide and the resin is sufficiently electron withdrawing that the peptidyl-OCH2-Pam-resin is 100 times more stable than the conventional peptidyl-OCH2-resin to cleavage of the ester bond by 50% trifluoroacetic acid in dichloromethane. Boc-Val-OCH2-Pam-resin, which was prepared by two routes, compared favorably with Boc-Val-OCH2-resin for synthesis of the model peptides leucylalanylglycylvaline and decalysylvaline. The greater acid stability of the Pam-resin is expected to result in much higher yields of large peptides prepared by solid-phase peptide synthesis.The solid support commonly used for solid-phase peptide synthesis,3 ie/T-butoxycarbonylaminoacyloxymethylpoly(styrene-co-divinylbenzene), is not completely stable under the acidic conditions required to remove the iert-butoxycarbonyl (Boc) group.4"7 Acidolysis of the benzyl ester link be-
Bei der Festphasen‐ Peptidsynthese gehen im allgemeinen einige der mit dem Hydroxymethyl‐poly‐(styrolco‐divinylbenzoD‐Harz (I) veresterten Peptidketten durch die Acidolyse verloren; dieser Verlust läßt sich jedoch durch Verwendung des Harzes (II) anstelle von (I) als Festträger minimieren: Die Pam‐Brücke zwischen Peptid und Harz ist gegenüber einer Spaltung der Esterbindung durch Trifluoressigsäure in CH2Cl2 100 mal stabiler als das konventionelle Peptidyl‐O(CH2 )‐Harz.
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