AMINO-ACIDS AND PEPTIDES .45. DEVELOPMENT OF A NEW N-PI-PROTECTING GROUP OF HISTIDINE, N-PI-(1-ADAMANTYLOXYMETHYL)-HISTIDINE, AND ITS EVALUATION FOR PEPTIDE-SYNTHESIS

Authors
OKADA Y WANG JD YAMAMOTO T MU Y YOKOI T
Citation
Y. Okada et al., AMINO-ACIDS AND PEPTIDES .45. DEVELOPMENT OF A NEW N-PI-PROTECTING GROUP OF HISTIDINE, N-PI-(1-ADAMANTYLOXYMETHYL)-HISTIDINE, AND ITS EVALUATION FOR PEPTIDE-SYNTHESIS, Journal of the Chemical Society. Perkin transactions. I, (17), 1996, pp. 2139-2143
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
17
Year of publication
1996
Pages
2139 - 2143
Database
ISI
SICI code
0300-922X(1996):17<2139:AAP.DO>2.0.ZU;2-X
Abstract
N-pi-(1-Adamantyloxymethyl)histidine, His(N-pi-1-Adom), is prepared an d its properties are examined. The 1-Adom group can be easily removed by trifluoroacetic acid and it is stable to 20% piperidine-dimethylfor mamide and 1 mol dm(-3) NaOH. His(N-pi-1-Adom) derivatives can suppres s racemization during coupling reactions. His(N-pi-1-Adom) can be used in solid-phase peptide synthesis in combination with fluoren-9-ylmeth oxycarbonyl as an N-alpha-protecting group. Thyrotropin-releasing horm one is successfully synthesized by using His(N-pi-1-Adom).