The Journal of organic chemistry

Synthesis of cyclic oligomers from histidine-derived building blocks using dynamic combinatorial chemistry

M Matsumoto, KM Nicholas

Index: Matsumoto, Masaomi; Nicholas, Kenneth M. Journal of Organic Chemistry, 2007 , vol. 72, # 24 p. 9308 - 9313

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Citation Number: 9

Abstract

Histidine-derived hydrazide acetal monomers (3-dimethoxymethylbenzoyl)-l-histidine methyl ester 1 and (3-dimethoxymethylbenzoyl)-τ-benzyl-l-histidine methyl ester 2 were prepared from a histidine methyl ester and a τ-benzyl-histidine methyl ester by N-acylation with 3- (dimethoxymethyl) benzoic acid (3) followed by hydrazinolysis. Acid-promoted hydrolysis of each acetal hydrazide initially produced a library of cyclic oligomers that eventually ...