Amino acids and peptides. L. Development of a novel N(π)-protecting group for histidine, N(π)-2-adamantyloxymethylhistidine, and its application to peptide synthesis

Article abstract of DOI:10.1248/cpb.45.452

N(α)-tert-Butyloxycarbonyl-N(π)-2-adamantyloxymethylhistidine, Boc- His(N(π)-2-Adom)-OH, was prepared by the reaction of Boc-His (N(τ)-Boc)- OMe with 2-adamantyloxymethyl chloride (2-Adom-Cl), followed by saponification. The 2-Adom group was stable to trifluoroacetic acid (TFA), 1 N NaOH and 20% piperidine/DMF and easily removed by 1M trifluoromethanesulfonic acid-thioanisole/TFA and HF. This new protecting group suppressed racemization during peptide synthesis and exhibited high solubility in organic solvents. It was applied to the synthesis of thyrotropin-releasing hormone (TRH) using both solution and solid-phase methods. The N(π)-2-Adom group can be used for peptide synthesis in combination with the tert-butyloxycarbonyl group as the N(α)-protecting group in both solution and solid-phase methods.

Full text of DOI:10.1248/cpb.45.452

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NII-Electronic Library Service

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NII-Electronic Library Service

NII-Electronic Library Service