Acid-labile histidine side-chain protection: the N(π)-t-butoxymethyl group

Abstract
N-(α)-Benzyloxycarbonyl-N(π)-t-butoxymethyl -L-histidine (1)and N(α)-fluoren-9-ylmethoxycarbonyl--N(π)-t-butoxymethyl-L-histidine(2)have been prepared and their use for the synthesis of peptides containing histidine residues has been demonstrated in two simple exercises; no difficulties were encountered, the base-and hydrogenolysis-resistant imidazole imidazole protecting group ultimately being removed by mild acidolysis.

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