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

✍ Scribed by H. C. Beyerman; J. S. Bontekoe

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
378 KB
Volume
81
Category
Article
ISSN
0165-0513

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✦ Synopsis

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 ^1,2^

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