Amino Acids and Peptides. L. Development of a Novel N. PI.-Protecting Group for Histidine, N. PI.-2-Adamantyloxymethylhistidine, and Its Application to Peptide …
Y Okada, J Wang, T Yamamoto, T YOKOI…
Index: Okada, Yoshio; Wang, Jidong; Yamamoto, Takeshi; Yokoi, Toshio; Mu, Yu Chemical and Pharmaceutical Bulletin, 1997 , vol. 45, # 3 p. 452 - 456
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Citation Number: 8
Abstract
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 1 M trifluoromethanesulfonic acid-thioanisole/TFA and HF. This new protecting group ...
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[Chemical and Pharmaceutical Bulletin, , vol. 45, # 3 p. 452 - 456]