Syntheses and reactions of functional polymers. XCIII. Syntheses of polymers containing the N‐(4‐hydroxy‐3‐nitrophenyl)succinimide structure in the chain and the use of these activated polymer esters of N‐blocked amino acids or peptides

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Abstract
Polymers containing the N‐(4‐hydroxy‐3‐nitrophenyl)succinimide residue were designed in order to achieve acyl activation of a reacting carboxylic acid in the solid phase. These polymers were prepared through the following three routes: (a) styrene was allowed to copolymerize with N‐(4‐hydroxy‐3‐nitrophenyl)‐ or N‐(4‐acetoxy‐3‐nitrophenyl)maleimide, (b) styrene was copolymerized with N‐(4‐acetoxyphenyl)maleimide in the presence of divinylbenzene (DVB), and the copolymer obtained was hydrolyzed and nitrated, (c) a copolymer of maleic anhydride and styrene was reacted with p‐aminophenol, followed by nitration. The polymers prepared by routes b and c were converted to the activated polymer esters of N‐blocked amino acids and peptides by using dicyclohexylcarbodiimide (DCC). The acylated polymers thus obtained were treated with amino acid esters and found to give peptides quantitatively without racemization.