The t??butoxy group, a novel hydroxyl??protecting group for use in peptide synthesis with hydroxy??amino acids

HC Beyerman, JS Bontekoe

Index: Beyerman,H.C.; Bontekoe,J.S. Recueil des Travaux Chimiques des Pays-Bas, 1962 , vol. 81, p. 691 - 698

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Citation Number: 55

Abstract

We have found a novel way of protecting the hydroxyl function in hydroxy- L-amino acids, making use of the t-butoxy group, which is readily split by acids, but not by bases. This group is introduced by acid-catalysed addition of isobutene to N-acylated hydroxy-L-amino acids. The blocking group is easily removed at or below room temperature with trifluoroacetic acid without racemization and without breaking peptide bonds 1,s. ... The hydroxy-L-amino acids serine, threonine, ...